Halogen Containing Reactant Patents (Class 568/437)
  • Patent number: 9498448
    Abstract: The present invention provides a process for purifying a monoterpene or sesquiterpene having a purity greater than about 98.5% (w/w). The process comprises the steps of derivatizing the monoterpene (or sesquiterpene) to produce a monoterpene (or sesquiterpene) derivative, separating the monoterpene (or sesquiterpene) derivative, and releasing the monoterpene (or sesquiterpene) from the derivative. Also encompassed by the scope of the present invention is a pharmaceutical composition comprising a monoterpene (or sesquiterpene) having a purity greater than about 98.5% (w/w). The purified monoterpene can be used to treat a disease such as cancer. The present monoterpene (or sesquiterpene) may be administered alone, or may be co-administered with radiation or other therapeutic agents, such as chemotherapeutic agents.
    Type: Grant
    Filed: September 2, 2015
    Date of Patent: November 22, 2016
    Assignee: NeOne Technologies, Inc.
    Inventors: Thomas Chen, Daniel Levin, Satish Puppali
  • Patent number: 9480659
    Abstract: The present invention provides a process for purifying a monoterpene or sesquiterpene having a purity greater than about 98.5% (w/w). The process comprises the steps of derivatizing the monoterpene (or sesquiterpene) to produce a monoterpene (or sesquiterpene) derivative, separating the monoterpene (or sesquiterpene) derivative, and releasing the monoterpene (or sesquiterpene) from the derivative. Also encompassed by the scope of the present invention is a pharmaceutical composition comprising a monoterpene (or sesquiterpene) having a purity greater than about 98.5% (w/w). The purified monoterpene can be used to treat a disease such as cancer. The present monoterpene (or sesquiterpene) may be administered alone, or may be co-administered with radiation or other therapeutic agents, such as chemotherapeutic agents.
    Type: Grant
    Filed: August 4, 2015
    Date of Patent: November 1, 2016
    Assignee: NeOnc Technologies, Inc.
    Inventors: Thomas Chen, Daniel Levin, Satish Puppali
  • Patent number: 9029606
    Abstract: A process for obtaining an industrially useful 2-chloromethylbenzaldehyde-containing liquid composition at a high yield is provided. More specifically, a process for producing 2-chloromethylbenzaldehyde comprising step (A) of mixing 1-dichloromethyl-2-chloromethylbenzene and sulfuric acid having a concentration of 84.5% by weight or more; and step (B) of mixing a mixture obtained in step (A) and water is provided.
    Type: Grant
    Filed: June 27, 2012
    Date of Patent: May 12, 2015
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masashi Takimoto, Tomonori Yamaoka, Yoshio Onogawa
  • Patent number: 8937200
    Abstract: A new process capable of producing a 2-(aryloxymethyl)benzaldehyde compound is provided. More particularly, a process for producing a 2-(aryloxymethyl)benzaldehyde compound represented by formula (2) comprising a step of hydrolyzing a compound represented by following formula (1); wherein X1 and X2 each represent independently a chlorine atom, a bromine atom or an iodine atom, Q1, Q2, Q3 and Q4 each represent independently a hydrogen atom or a halogen atom, and Ar represents a phenyl group optionally having a substituent.
    Type: Grant
    Filed: June 27, 2012
    Date of Patent: January 20, 2015
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masaji Hirota, Masashi Takimoto, Tomonori Yamaoka, Yoshio Onogawa
  • Publication number: 20140228579
    Abstract: The present application relates to methods for the catalytic reduction of acid chlorides and/or imidoyl chlorides. The methods comprise reacting the acid chloride or imidoyl chloride with a silane reducing agent in the presence of a catalyst such as [Cp(Pri3P)Ru(NCMe)2]+[PF6]?.
    Type: Application
    Filed: September 11, 2013
    Publication date: August 14, 2014
    Applicant: Brock Unviersity
    Inventors: Georgii Nikonov, Dmitry Gutsulyak, Sun Hwa Lee
  • Publication number: 20140221695
    Abstract: A new process capable of producing a 2-(aryloxymethyl)benzaldehyde compound is provided. More particularly, a process for producing a 2-(aryloxymethyl)benzaldehyde compound represented by formula (2) comprising a step of hydrolyzing a compound represented by following formula (1); wherein X1 and X2 each represent independently a chlorine atom, a bromine atom or an iodine atom, Q1, Q2, Q3 and Q4 each represent independently a hydrogen atom or a halogen atom, and Ar represents a phenyl group optionally having a substituent.
    Type: Application
    Filed: June 27, 2012
    Publication date: August 7, 2014
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Masaji Hirota, Masashi Takimoto, Tomonori Yamaoka, Yoshio Onogawa
  • Publication number: 20140187822
    Abstract: A process for obtaining an industrially useful 2-chloromethylbenzaldehyde-containing liquid composition at a high yield is provided. More specifically, a process for producing 2-chloromethylbenzaldehyde comprising step (A) of mixing 1-dichloromethyl-2-chloromethylbenzene and sulfuric acid having a concentration of 84.5% by weight or more; and step (B) of mixing a mixture obtained in step (A) and water is provided.
    Type: Application
    Filed: June 27, 2012
    Publication date: July 3, 2014
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Masashi Takimoto, Tomonori Yamaoka, Yoshio Onogawa
  • Patent number: 8742187
    Abstract: The method of the present invention provides a high yield pathway to 2,5-dimethylhexadiene from renewable isobutanol, which enables economic production of renewable p-xylene (and subsequently, terephthalic acid, a key monomer in the production of PET) from isobutanol. In addition, the present invention provides methods for producing 2,5-dimethylhexadiene from a variety of feed stocks that can act as “equivalents” of isobutylene and/or isobutyraldehyde including isobutanol, isobutylene oxide, and isobutyl ethers and acetals. Catalysts employed in the present methods that produce 2,5-dimethylhexadiene can also catalyze alcohol dehydration, alcohol oxidation, epoxide rearrangement, and ether and acetal cleavage.
    Type: Grant
    Filed: April 19, 2012
    Date of Patent: June 3, 2014
    Assignee: GEVO, Inc.
    Inventors: Thomas Jackson Taylor, Joshua D. Taylor, Matthew W. Peters, David E. Henton
  • Patent number: 8692026
    Abstract: A new synthesis of 4-bromo-2-methoxybenzaldehyde is reported from 1,4 dibromo 2-fluorobenzene. First, 2-fluoro-4-bromobenzaldehyde is prepared through metal halogen exchange and formylation with a formyl source at 0° C. After crystallization, this intermediate is reacted with methanol in the presence of potassium carbonate. Subsequently, 4-bromo-2-methoxy-benzaldehyde is crystallized.
    Type: Grant
    Filed: July 1, 2011
    Date of Patent: April 8, 2014
    Assignee: Albemarle Corporation
    Inventors: Thierry J. Giard, Vincent L. Mutterer, Christophe Durvaux
  • Publication number: 20130259804
    Abstract: The present invention relates to improved radiotracer imaging agent compositions, which comprises 18F-labelled biological targeting moieties, wherein impurities which affect imaging in vivo are identified and suppressed. Also provided are radiopharmaceuticals comprising said improved compositions, together with radiofluorinated aldehyde compositions useful in preparing said radiotracer compositions. The invention also includes methods of imaging and/or diagnosis using the radiopharmaceutical compositions described.
    Type: Application
    Filed: December 9, 2011
    Publication date: October 3, 2013
    Applicant: GE HEALTHCARE LIMITED
    Inventors: Torgrim Engell, Julian Grigg, Dimtrios Mantzilas
  • Patent number: 8399710
    Abstract: An alkali metal fluoride dispersion of an alkali metal fluoride and an aprotic organic solvent is obtainable by (A) separating a liquid phase from an alkali metal fluoride dispersion comprising an alcohol solvent and an alkali metal fluoride, and mixing the separated liquid phase with an aprotic organic solvent having a boiling point of 85° C. or higher at normal pressure; (B) obtaining a mixture containing the alkali metal fluoride by (b1) concentrating the mixture containing the alkali metal fluoride to obtain a concentrated fraction and a concentrated residue; (b2) mixing a residue of the alkali metal fluoride dispersion with the concentrated fraction obtained in (b1); and (b3) separating a liquid phase from the mixture containing an alkali metal fluoride obtained in (b2) and mixing the separated liquid phase with the concentrated residue; and (C) removing the alcohol solvent from the mixture containing the alkali metal fluoride.
    Type: Grant
    Filed: August 27, 2008
    Date of Patent: March 19, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Koji Hagiya
  • Patent number: 8350091
    Abstract: A potassium fluoride dispersion essentially consisting of potassium fluoride and an aprotic organic solvent having a boiling point higher than that of methanol, which is obtainable by mixing a mixture containing potassium fluoride and 5 to 50 parts by weight of methanol per 1 part by weight of potassium fluoride with the aprotic organic solvent followed by concentrating the obtained mixture, and a process for producing a fluorine-containing organic compound comprising contacting an organic compound having at least one group capable of being substituted nucleophilically with a fluorine atom with the potassium fluoride dispersion.
    Type: Grant
    Filed: December 30, 2011
    Date of Patent: January 8, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Hagiya, Kazuaki Sasaki
  • Patent number: 8338649
    Abstract: The invention relates to a method for the production of an aromatic carbonyl compound by the oxidation of a methyl group or methylene group bonded to the aromatic group in which the aromatic substance is reacted in the presence of an oxidizing agent and a sulphoxide, a sulphoxide being selected for the oxidation of a specific aromatic substance whose ionization potential, in terms of magnitude, differs from the ionization potential of the aromatic substance to be oxidized by a maximum of ±0.25 eV.
    Type: Grant
    Filed: September 2, 2008
    Date of Patent: December 25, 2012
    Assignee: Weylchem Frankfurt GmbH
    Inventors: Klaus Forstinger, Thomas Sommer, Daniel Decker, Andreas Martin, Angela Köckritz, Michael Kant, Alexander Hofmann
  • Patent number: 8258349
    Abstract: A benzaldehyde acetal compound of formula (3): (wherein Q represents a hydrogen atom or a halogen atom, Ar represents a phenyl group optionally substituted with at least one selected from the group consisting of alkyl groups having 1 to 4 carbon atoms and halogen atoms, and R represents an alkyl group having 1 to 4 carbon atoms).
    Type: Grant
    Filed: January 30, 2009
    Date of Patent: September 4, 2012
    Assignee: Suitomo Chemical Company, Limited
    Inventor: Koichi Nakazawa
  • Publication number: 20120165548
    Abstract: Processes for the preparation of Silodosin and its intermediates comprising reductive amination of compound of Formula (VIII) with a compound of Formula (VII) or a compound of Formula (XV) in a suitable solvent using a reducing agent.
    Type: Application
    Filed: September 13, 2010
    Publication date: June 28, 2012
    Applicant: SANDOZ AG
    Inventors: Shreerang Joshi, Sachin Bhuta, Sanjay Talukdar, Sudhir Sawant, Deepak Venkataraman, Abhinay Pise, Shashikant Metkar, Dattatraya Chavan, Parven Kumar Luthra
  • Patent number: 7994367
    Abstract: A method is provided for producing a benzaldehyde compound represented by the formula (4): wherein Q1 and Q2 represent an alkyl group etc., n represents 1 or 2, and Ar represents a phenyl group etc., including the steps of reacting a compound represented by the formula (3): wherein X1 represents a chlorine atom etc., and Q1, Q2, n and Ar are respectively the same meaning as above, with magnesium metal to obtain a Grignard compound and then reacting the obtained Grignard compound with a formylating agent.
    Type: Grant
    Filed: May 14, 2008
    Date of Patent: August 9, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Koichi Nakazawa
  • Publication number: 20110098489
    Abstract: A method of producing a corresponding acetal compound which comprises reacting a benzal halide compound represented by formula (1) (wherein, Q represents a hydrogen atom or a halogen atom, X represents a halogen atom, and Ar represents a phenyl group optionally substituted with at least one group selected from the group consisting of alkyl groups having 1 to 4 carbon atoms and halogen atoms.) and an alcohol compound in the presence of at least one alkaline earth metal compound selected from the group consisting of alkaline earth metal oxides, alkaline earth metal hydroxides and alkaline earth metal carbonates.
    Type: Application
    Filed: June 9, 2009
    Publication date: April 28, 2011
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Yoshio Onogawa, Kazuyoshi Yamanaka, Masaji Hirota
  • Patent number: 7851659
    Abstract: A method is provided for producing a benzaldehyde compound represented by the formula (2): wherein Q1 and Q2 represent a hydrogen atom etc., including the step of reacting a compound represented by the formula (1): wherein X represents a chlorine atom etc., and Q1 and Q2 are respectively the same meaning as above, with a secondary nitroalkane and a base in the presence of an alkali metal iodide.
    Type: Grant
    Filed: May 14, 2008
    Date of Patent: December 14, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Koichi Nakazawa
  • Publication number: 20100312017
    Abstract: The invention relates to a method for the production of an aromatic carbonyl compound by the oxidation of a methyl group or methylene group bonded to the aromatic group in which the aromatic substance is reacted in the presence of an oxidising agent and a sulphoxide, a sulphoxide being selected for the oxidation of a specific aromatic substance whose ionisation potential, in terms of magnitude, differs from the ionisation potential of the aromatic substance to be oxidised by a maximum of ±0.25 eV.
    Type: Application
    Filed: September 2, 2008
    Publication date: December 9, 2010
    Inventors: Klaus Forstinger, Thomas Sommer, Daniel Decker, Andreas Martin, Angela Köckritz, Michael Kant, Alexander Hofmann
  • Publication number: 20100292513
    Abstract: A benzaldehyde acetal compound of formula (3): (wherein Q represents a hydrogen atom or a halogen atom, Ar represents a phenyl group optionally substituted with at least one selected from the group consisting of alkyl groups having 1 to 4 carbon atoms and halogen atoms, and R represents an alkyl group having 1 to 4 carbon atoms).
    Type: Application
    Filed: January 30, 2009
    Publication date: November 18, 2010
    Inventor: Koichi Nakazawa
  • Patent number: 7790931
    Abstract: A process for preparing tetrafluorobenzene carbaldehyde alkyl acetal represented by the following formula (II), comprising reducing tetrafluorocyanobenzene represented by the following formula (I) with a metal catalyst containing a platinum group metal in the presence of an alkyl alcohol represented by R—OH (R is an alkyl group of 1 to 4 carbon atoms) and an acid; (I) wherein m is 1 or 2, n is 0 or 1, and m+n is 2, (II) wherein m and n are the same as those in the formula (I), and R is an alkyl group of 1 to 4 carbon atoms.
    Type: Grant
    Filed: June 12, 2006
    Date of Patent: September 7, 2010
    Assignee: Showa Denko K.K.
    Inventors: Haruhiko Ikeda, Hideo Miyata, Katsutoshi Ohno, Katsuro Urakawa
  • Publication number: 20100210879
    Abstract: A method is provided for producing a benzaldehyde compound represented by the formula (4): wherein Q1 and Q2 represent an alkyl group etc., n represents 1 or 2, and Ar represents a phenyl group etc., including the steps of reacting a compound represented by the formula (3): wherein X1 represents a chlorine atom etc., and Q1, Q2, n and Ar are respectively the same meaning as above, with magnesium metal to obtain a Grignard compound and then reacting the obtained Grignard compound with a formylating agent.
    Type: Application
    Filed: May 14, 2008
    Publication date: August 19, 2010
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Koichi Nakazawa
  • Publication number: 20100130758
    Abstract: Disclosed are a catalyst including a hydrotalcite and, immobilized on a surface thereof, particles of at least one metal selected from the group consisting of Cu, Ag, and Au; a method for producing a carbonyl compound through dehydrogenation of an alcohol in the presence of the catalyst; and a method for producing a carbonyl compound through dehydrogenation of an alcohol in the presence of a catalyst including a hydrotalcite and, immobilized on a surface thereof, particles of a metal, in which dehydrogenation is performed in the absence of oxygen.
    Type: Application
    Filed: March 9, 2007
    Publication date: May 27, 2010
    Inventors: Kiyotomi Kaneda, Noritsugu Yamasaki
  • Patent number: 7718827
    Abstract: The present invention relates to a process for preparing aldehydes or ketones using an alkali metal hypochlorite or an alkaline earth metal hypochlorite in the presence of a ruthenium catalysts.
    Type: Grant
    Filed: June 28, 2006
    Date of Patent: May 18, 2010
    Assignee: Saltigo GmbH
    Inventors: Wolfgang Mägerlein, Angela Köckritz, Andrea Dittmar, Michael Sebek
  • Patent number: 7714173
    Abstract: The present invention relates to a method for preparing high-purity terephthalaldehyde which comprises re-crystallizing terephthalaldehyde crystals containing impurities, using an anti-solvent. Specifically, the present invention relates to a method for preparing terephthalaldehyde which comprises dissolving low-purity terephthalaldehyde prepared by a conventional method in dimethylsulfoxide and then re-crystallizing the solution, using water as an anti-solvent. The present invention is not only environment-friendly because it uses water only as an anti-solvent, but also economical because it may simply prepare high-purity terephthalaldehyde in a short time.
    Type: Grant
    Filed: June 14, 2007
    Date of Patent: May 11, 2010
    Assignee: LG Chem, Ltd.
    Inventors: Seong-Hoon Kang, In-Kyu Park, Jong-Suh Park, Young-Dae Kim, Jong-Hyun Chae
  • Patent number: 7619123
    Abstract: The present invention provides novel methods for stabilizing lithiated halogen-substituted aromatic compounds. In particular, the method is useful for the preparation of 2-methoxy-5,6-difluorobenzaldehyde, an important intermediate for the preparation of [4-amino-2-(1-methanesulfonylpiperidin-4-ylamino)pyrimidin-5-yl](2,3-difluoro-6methoxyphenyl)methanone, a potent and selective inhibitor of CDK4/Cyclin D1, CDK2/Cyclin E and CDK1/Cyclin B. The method is also useful for stabilizing other lithiated halogen-substituted aromatic compounds and is particularly useful for scale up reactions where the exothermic nature of the reaction can lead to reaction runway.
    Type: Grant
    Filed: October 24, 2008
    Date of Patent: November 17, 2009
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Yaohui Ji, Thimma Rawalpally
  • Publication number: 20090131660
    Abstract: 3-[4-(1,1-Dimethyl-propyl)-phenyl]-2-methyl-propionaldehyde and cis-4-{3-[4-(1,1-dimethyl-propyl)-phenyl]-2-methyl-propyl}-2,6-dimethyl-morpholine (Amorolfine) are synthesized, first by Heck reacting a compound of general formula (VI): with 2-methyl-prop-2-en-1-ol of formula (VII): in the presence of a palladium catalyst and a base, in a solvent selected from among N,N-dimethylformamide, polar protic and non-polar organic solvents, and at a temperature ranging from 60° C. to 150° C., and then conducting an amino reduction by reacting the 3-[4-(1,1-dimethyl-propyl)-phenyl]-2-methyl-propionaldehyde of formula (II) with cis-2,6-dimethyl morpholine of formula (IV): in the presence of a reducing agent and in a solvent.
    Type: Application
    Filed: October 3, 2008
    Publication date: May 21, 2009
    Applicant: GALDERMA S.A.
    Inventors: JEAN-GUY BOITEAU, BRANISLAV MUSICKI
  • Patent number: 7479575
    Abstract: The present invention is related to a new synthesis for preparing para-phenyl alkynyl benzaldehyde of general formula (I). The compounds of formula (I) are useful building blocks, in particular in the synthesis of electrically conducting polymers. R is selected from the group consisting of C1-C12-alkyl, C1-C12-alkyl aryl, C1-C12-alkyl heteroaryl, C2-C12-alkenyl, C2C12-alkenyl aryl, C2-C12-alkenyl heteroaryl, C2-C12-alkynyl, C2-C12-alkynyl aryl, C2-C12-alkynyl heteroaryl, C3-C8-cycloalkylC1-C12-alkyl-C3-C8-cycloalkyl, C1-C12-alkoxy, aryl, heteroaryl, halides.
    Type: Grant
    Filed: October 12, 2004
    Date of Patent: January 20, 2009
    Assignee: Laboratoires Serono SA
    Inventors: Dominique Swinnen, Danig Pohin
  • Patent number: 7411099
    Abstract: The present invention provides a liquid phase oxidation of toluene by using catalyst containing manganese (Manganese II acetate) in presence of Lewis acid (Stannous (II) chloride) and a bromide promoter (NaBr), at a temperature of 120° C. and at a pressure of air in the range of 70-400 psig, in presence of carboxylic acid (acetic acid), as a solvent, to obtain high selectivity to benzaldehyde (76%). High activity was obtained with minimum byproducts such as benzoic acid, benzyl alcohol and benzyl acetate.
    Type: Grant
    Filed: September 20, 2006
    Date of Patent: August 12, 2008
    Assignee: Council of Scientific & Industrial Research
    Inventors: Raghunath Vitthal Chaudhari, Kalpendra Baburao Rajurkar, Sunil Sopana Tonde, Vilas Hari Rane
  • Patent number: 7402709
    Abstract: A new high-yield, easily industrialized process for synthesizing compounds of formula (IV), in which X1 and X2, the same or different, are linear or branched C1-C8 alkyls, n and m are 0, 1 or 2, with the proviso that n and m are not simultaneously 0; or (OX1)n and (OX2)m taken together form an O-T-O group where T is chosen from —CH2—, —CH2CH2, —CH2CH2CH2—, —C(CH3)2—. The process comprises treating a chloromethyl derivative (I) with an alkaline acetate to form the intermediate acetylderivative (II); the intermediate (II) is to hydrolysed to form the alcohol (III); the alcohol (III) is then oxidised in the presence of air and catalysts to obtain the desired derivative (IV). The process runs its course within a short period of time, with high yields and high selectivity; in addition, the process does not require purification and separation of the intermediates and can therefore be favourably conducted in a single batch.
    Type: Grant
    Filed: October 28, 2004
    Date of Patent: July 22, 2008
    Assignee: Endura S.p.A.
    Inventors: Valerio Borzatta, Elisa Capparella, Carlotta Gobbi, Elisa Poluzzi
  • Publication number: 20080108849
    Abstract: The present invention is related to a new synthesis for preparing para-phenyl alkynyl benzaldehyde of general formula (I). The compounds of formula (1) are useful building blocks, in particular in the synthesis of electrically conducting polymers. R is selected from the group consisting of C1-C12-alkyl, C1-C12-alkyl aryl, C1-C12-alkyl heteroaryl, C2-C12-alkenyl, C2C12-alkenyl aryl, C2-C12-alkenyl heteroaryl, C2-C12-alkynyl, C2-C12-alkynyl aryl, C2-C12-alkynyl heteroaryl, C3-C8-cycloalkylC1-C12--alkyl-C3-C8-cycloalkyl, C1-C12-alkoxy, aryl, heteroaryl, halides.
    Type: Application
    Filed: October 12, 2004
    Publication date: May 8, 2008
    Applicant: APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.
    Inventors: Dominique Swinnen, Danig Pohin
  • Patent number: 7342138
    Abstract: A process for producing an aromatic aldehyde compound represented by a general formula (3): (wherein R? and n are as defined below), which comprises reacting a benzyl compound represented by a general formula (1): (wherein R may represents hydrogen atom, n represents an integer of 1 to 6, and R? may be the same or different and represent a hydrogen atom or an alkyl gorup, an alkyl group or a phenyl group which may have a substituent) with an oxy-compound of bromine represented by the formula (2): MBrOm??(2) (wherein M represents a hydrogen atom or a metal atom, and m represents an integer of 1 to 3) in the presence of an acid catalyst. According to this method, an aromatic aldehyde compound can be produced in high selectivity by a simple operation without using an expensive catalyst or transition metal.
    Type: Grant
    Filed: August 27, 2003
    Date of Patent: March 11, 2008
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventor: Kentaro Kawazoe
  • Patent number: 7241925
    Abstract: In the production method of the invention, a halogen-substituted aromatic compound is reacted with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride into a corresponding halogen-substituted aromatic aldehyde. By the use of hydrogen fluoride and boron trifluoride, the para position to halogen atom is selectively formylated to provide the halogen-substituted aromatic aldehyde in high yields in a short reaction time even at temperatures lower than room temperature.
    Type: Grant
    Filed: December 15, 2004
    Date of Patent: July 10, 2007
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kinji Kato, Junya Nishiuchi, Mitsuharu Kitamura
  • Patent number: 7189882
    Abstract: The present invention provides an improved process for the liquid phase oxidation of toluene to benzaldehyde with high selectivity and good activity in an organic acid medium using a catalyst system consisting of transition metal/metals and bromide as a promoter in the presence of lean oxygen.
    Type: Grant
    Filed: December 23, 2005
    Date of Patent: March 13, 2007
    Assignee: Council of Scientific and Industrial Research
    Inventors: Raghunath Vittal Chaudhari, Vilas Hari Rane, Amit Arwind Deshmukh, Sunil Sadashiv Divekar
  • Patent number: 7122705
    Abstract: Processes for coupling phenol and cycloalkyls including combining an optionally substituted phenol, a cycloalkyl substituted with a leaving group, carbonate salt, tetrahydrofuran, and an optional phase transfer agent are provided. Also provided are processes for preparing 3-cyclopentyloxy-4-methoxybenzaldehyde by combining 3-hydroxy-4-methoxybenzaldehyde, a cyclopentyl compound, a carbonate salt, a solvent, and an optional phase transfer agent.
    Type: Grant
    Filed: April 7, 2005
    Date of Patent: October 17, 2006
    Assignee: Wyeth
    Inventors: Bogdan Kazimierz Wilk, Nalukui Mwisiya, Jean Louise Helom
  • Patent number: 7087789
    Abstract: A novel, convenient and efficient method for trifluoromethylation of substrate compounds is disclosed. Particularly, alkoxide and hydroxide induced nucleophilic trifluoromethylation of carbonyl compounds, disulfides and other electrophiles, using phenyl trifluoromethyl sulfone PhSO2CF3 (or sulfoxide PhSOCF3) is disclosed. A method of both symmetrical and unsymmetrical anti-2,2-difluoropropan-1,3-diols with high diastereoselectivity (up to 94% de) is disclosed using difluoromethyl phenyl sulfone. This unusual type of high diastereoselectivity was obtained via an intramolecular charge-charge repulsion effect rather than the traditional steric control (based on the Cram's rule). Thus, difluoromethyl phenyl sulfone can be used as a novel difluoromethylene dianion species (“?CF2?”), which can couple two electrophiles (such as diphenyl disulfide or non-enolizable aldehydes) to give new difluoromethylenated products.
    Type: Grant
    Filed: January 12, 2004
    Date of Patent: August 8, 2006
    Assignee: University of Southern California
    Inventors: G. K. Surya Prakash, Jinbo Hu, George A. Olah
  • Patent number: 7078572
    Abstract: The invention is a process for the preparation of compounds of the Formula I: where R1, R2, R3, R4 and R5 are defined in the specification, which are intermediates useful for the preparation of tubulin inhibitors which are useful in the treatment of cancer.
    Type: Grant
    Filed: August 11, 2005
    Date of Patent: July 18, 2006
    Assignee: Wyeth Holdings Corporation
    Inventor: John Thomas Kendall
  • Patent number: 6933405
    Abstract: The present invention is a user- and eco-friendly hypervalent iodine reagent (mIBX) capable of selectively oxidizing allylic and benzylic alcohols in water and other eco-friendly solvents and having generally the following structure: Allylic and benzylic alcohols are cleanly oxidized to the corresponding carbonyl compounds in water or water-THF mixtures, or other mixtures, using a water-soluble o-iodoxybenzoic acid derivative of the present invention.
    Type: Grant
    Filed: July 31, 2003
    Date of Patent: August 23, 2005
    Assignee: Board of Trustees of Western Illinois University
    Inventors: Thottumkara K. Vinod, Arun P. Thottumkara
  • Patent number: 6891069
    Abstract: Disclosed herein are methods of synthesizing a 4-substituted-benzene-1,2-carbaldehyde. In one aspect, a method may include reacting a 4-substituted-1,2-bis(dibromomethyl) benzene with sulfuric acid to form a reaction product, introducing a solid sodium bicarbonate into the reaction product, and hydrolyzing the reaction product to form a 4-substituted-benzene-1,2-carbaldehyde, after introducing the bicarbonate.
    Type: Grant
    Filed: January 30, 2004
    Date of Patent: May 10, 2005
    Assignee: Ethicon, Inc.
    Inventors: Peter C. Zhu, Der-Haw Wang
  • Patent number: 6881866
    Abstract: In the process of the present invention, a polyalkyl-substituted aromatic aldehyde is produced by the formylation of a corresponding polyalkyl-substituted aromatic compound with carbon monoxide in the presence of hydrogen fluoride/boron trifluoride catalyst. By limiting the amount of hydrogen fluoride to a specific range, the formylation rapidly proceeds under mild conditions without causing the precipitation of solid matters even when the starting polyalkyl-substituted aromatic compound has alkyl groups on both the carbon atoms adjacent to the site to be formylated.
    Type: Grant
    Filed: July 9, 2003
    Date of Patent: April 19, 2005
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kinji Kato, Tsuyoshi Hatakeyama, Mitsuharu Kitamura
  • Publication number: 20040230079
    Abstract: A novel, convenient and efficient method for trifluoromethylation of substrate compounds is disclosed. Particularly, alkoxide and hydroxide induced nucleophilic trifluoromethylation of carbonyl compounds, disulfides and other electrophiles, using phenyl trifluoromethyl sulfone PhSO2CF3 (or sulfoxide PhSOCF3) is disclosed. A method of both symmetrical and unsymmetrical anti-2,2-difluoropropan-1,3-diols with high diastereoselectivity (up to 94% de) is disclosed using difluoromethyl phenyl sulfone. This unusual type of high diastereoselectivity was obtained via an intramolecular charge-charge repulsion effect rather than the traditional steric control (based on the Cram's rule). Thus, difluoromethyl phenyl sulfone can be used as a novel difluoromethylene dianion species (“−CF2−”), which can couple two electrophiles (such as diphenyl disulfide or non-enolizable aldehydes) to give new difluoromethylenated products.
    Type: Application
    Filed: January 12, 2004
    Publication date: November 18, 2004
    Inventors: G.K.Surya Prakash, Jinbo Hu, George A. Olah
  • Patent number: 6811832
    Abstract: Compounds of the formula (I): in which X1=H or F, X2=H or F, and Y=Cl, Br or I, are prepared by reacting, in a solvent or solvent mixture at a temperature below −60° C., a halobenzene of the formula (II) with an organic lithium compound and then with a formyl equivalent of the formula (III): and may be used as starting materials for preparing agrochemicals, electronic materials and pharmaceuticals.
    Type: Grant
    Filed: May 10, 2001
    Date of Patent: November 2, 2004
    Assignee: Clariant GmbH
    Inventors: Rainer Wingen, Wolfgang Schmidt
  • Patent number: 6677479
    Abstract: Compounds of the formula (I) and also process for preparing them where substituents X1, X2, Y and Z are defined as follows: X1 is H or F X2 is H or F Y is CI, Br, or I Z is CHO or COOH or CN n is 0 or 1 and also their use as starting material for preparing agrochemicals, electronics materials and pharmaceuticals.
    Type: Grant
    Filed: November 12, 2002
    Date of Patent: January 13, 2004
    Assignee: Clariant Finance LBVI Limited
    Inventors: Wolfgang Schmidt, Rainer Wingen
  • Patent number: 6624336
    Abstract: The present invention relates to a process by a series of reactions using tetrafluorocyanobenzens as material for producing tetrafluorobenzenemethanols, tetrafluorobenzenecarbaldehyde dialkylacetals and tetrafluorobenzenecarbaldehydes in a high purity and a high yield which are useful as intermediates in the production of cyclopropanecarboxylic acid esters having insecticidal action, and also relates to a novel tetrafluorobenzenecarbaldehyde dimethylacetal.
    Type: Grant
    Filed: November 5, 2001
    Date of Patent: September 23, 2003
    Assignee: Showa Denko K.K.
    Inventors: Toru Sasaki, Tetsuhiro Furukawa, Toru Yoshida, Yutaka Ohnishi, Hiroyuki Monzen, Hideo Miyata, Kohei Morikawa
  • Patent number: 6624331
    Abstract: A process for producing benzyloxyacetaldehyde which comprises oxidizing 2-benzyloxyethanol with hypochlorous acid in the presence of a nitroxy radical having the general formula (I) wherein R represents a hydrogen atom, an acyloxy group, an alkoxyl group or an aralkyloxy group.
    Type: Grant
    Filed: September 27, 2001
    Date of Patent: September 23, 2003
    Assignee: Kuraray Co., Ltd.
    Inventors: Masahiro Torihara, Kensuke Nagashima, Koichi Kanehira, Yoshin Tamai
  • Patent number: 6608229
    Abstract: A simplified process for oxidizing starch and other polysaccharides in an aqueous solution or suspension using hypochlorite in the presence of a catalytic amount of a nitroxyl compound is described. The oxidation is process is bromide-free and is carried out at a pH between 7 and 8.3 and at a temperature between 15 and 25° C.
    Type: Grant
    Filed: April 25, 2001
    Date of Patent: August 19, 2003
    Assignee: SCA Hygiene Products Zeist B.V.
    Inventors: Petter Bragd, Arie Cornelis Besemer, Jeffrey Wilson Thornton
  • Patent number: 6596906
    Abstract: The invention relates to a particularly advantageous preparation of fluorine-containing benzaldehydes by reacting a corresponding aromatic acid chloride with hydrogen in the presence of a supported palladium catalyst and a catalyst moderator.
    Type: Grant
    Filed: September 21, 2001
    Date of Patent: July 22, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Käthe Baumann, Albrecht Marhold
  • Publication number: 20030125583
    Abstract: The invention relates to a particularly advantageous preparation of fluorine-containing benzaldehydes by reacting a corresponding aromatic acid chloride with hydrogen in the presence of a supported palladium catalyst and a catalyst moderator.
    Type: Application
    Filed: January 30, 2003
    Publication date: July 3, 2003
    Inventors: Kathe Baumann, Albrecht Marhold
  • Patent number: 6518419
    Abstract: Primary alcohols, especially in carbohydrates, can be selectively oxidized to aldehydes and carboxylic acids in a low-halogen process by using a peracid in the presence of a catalytic amount of a di-tertiary-alkyl nitroxyl (TEMPO) and a catalytic amount of halide. The halide is preferably bromide and the process can be carried out at nearly neutral to moderately alkaline pH (5-11). The peracid can be produced or regenerated by means of hydrogen peroxide or oxygen. The process is advantageous for producing uronic acids and for introducing aldehyde groups which are suitable for crosslinking and derivatization.
    Type: Grant
    Filed: November 7, 2000
    Date of Patent: February 11, 2003
    Assignee: Nederlandse Organisatie voor Toegepast-Natuurwetenschappelijk Onderzoek TNO
    Inventors: Jan Pieter Van Der Lugt, Jan Matthijs Jetten, Arie Cornelis Besemer, Hendrik Arend Van Doren
  • Patent number: 6476279
    Abstract: Disclosed are methods of producing fluorinated alcohols which find particular use in the syntheses of pharmaceutical drugs. The methods comprise generally, the steps of (a) reacting a halogenated alkane with an alkyl vinyl ether to form an unsaturated halogenated aldehyde; (b) reducing the unsaturated halogenated aldehyde to form an unsaturated halogenated alcohol; and (c) reducing the unsaturated halogenated alcohol to form a fluorinated alcohol.
    Type: Grant
    Filed: January 12, 2001
    Date of Patent: November 5, 2002
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Andrew Joseph Poss