Abstract: A method is provided for making an enantiomerically pure of the formula: in which R and R′ represent C1?C10 alkyl, C2?C10 alkenyl or C3?C10 cycloalkyl and the wedges signify (S)- or (R)-stereochemistry, the substituents in compound (II) being trans. Conjugate addition is carried out between an organometallic nucleophile that provides a group R as defined above and (R)-4-acetoxycyclopent-2-en-1-one, (S)-4-acetoxycyclopent-2-en-1-one or a similar compound in which acetoxy is replaced by another leaving group to give, e.g.
Type:
Application
Filed:
February 5, 2003
Publication date:
October 2, 2003
Inventors:
David Clive Blakemore, Justin Stephen Bryans
Abstract: The invention relates to a method for the 1,3 dipolar cycloaddition of organic compounds, characterised in that the reaction is carried out in a microreactor.
Abstract: A process is provided for the preparation of cyclohexene derivatives of general formula I or II:
in which the substituents R1 and R2 independently of one another are defined as follows:
R2 is OH or a protective group convertible to a hydroxyl group by hydrolysis,
R3 and R4 are hydrogen or C1-C4-alkyl, and
R5 is hydrogen or C1-C4-acyl,
by the reduction or alkyne compounds of general formula III or IV:
wherein the reducing agent used is at least one salt of hyposulfurous acid or hydroxymethanesulfinic acid or a mixture of at least one salt of hyposulfurous acid and at least one salt of hydroxymethanesulfinic acid.
Type:
Grant
Filed:
August 14, 2002
Date of Patent:
July 8, 2003
Assignee:
BASF Aktiengesellschaft
Inventors:
Johannes Grimmer, Thomas Müller, Volker Bomm
Abstract: Process for the preparation of 2,2,4,4-tetrasubstituted 1,3,5-cyclohexanetriones of the formula I,
by reaction of a cyclobutane-1,3-dione of the formula II
with an O or N nucleophile and a silylating reagent, and subsequent acetylation and cyclization.
Type:
Grant
Filed:
November 29, 2001
Date of Patent:
May 6, 2003
Assignee:
BASF Aktiengesellschaft
Inventors:
Roland Götz, Norbert Götz, Matthias Witschel, Michael Rack
Abstract: A method and apparatus for the production of ketones via a one-step synthesis from aldehydes. In the method of the invention, an aldehyde, a carboxylic acid, and a source of oxygen, such as water, are allowed to react in the vapor phase in a catalytic tube reactor. Asymmetrical ketones, such as methyl cyclopropyl ketone, are particularly desirable reaction products.
Type:
Grant
Filed:
October 17, 2001
Date of Patent:
April 8, 2003
Assignee:
EagleView Technologies, Inc.
Inventors:
Jack S. Warren, David R. Westphal, Steve J. Zoubek
Abstract: Acid addition salts of imidazolidinones are provided as catalysts for transforming a functional group within a first reactant by reaction with a second reactant. Exemplary first reactants are &agr;,&bgr;-unsaturated carbonyl compounds such as &agr;,&bgr;-unsaturated ketones and &agr;,&bgr;-unsaturated aldehydes. Chiral imidazolidinone salts can be used to catalyze enantioselective reactions, such that a chiral product is obtained from a chiral or achiral starting material in enantiomerically pure form.
Type:
Grant
Filed:
July 30, 2001
Date of Patent:
February 4, 2003
Assignee:
The Regents of the University of California
Inventors:
David W. C. MacMillan, Kateri A. Ahrendt
Abstract: A process for efficiently producing a 2-alkyl-2-cyclopentenone comprising reacting an amine and a hydrogen halide, which are present in a ratio ranging from 1.1:1 to 5:1, with a 2-alkylidene cyclopentanone to carry out an isomerization reaction. A process for producing a jasmonate derivative comprising reacting a 2-alkyl-2-cyclopentenone with a malonic acid diester.
Abstract: Process for the production of 2,2,6-trimethylcyclohexane-1,4-dione by epoxidation of &bgr;-isophorone with organic percarboxylic acids at a water content below 5 wt.-% and subsequent isomerization of the mixture of &bgr;-isophorone epoxide and hydroxyisophorone.
Type:
Application
Filed:
February 28, 2002
Publication date:
November 7, 2002
Inventors:
Steffen Krill, Klaus Huthmacher, Sylvain Perrin
Abstract: The present invention is directed to cyclopropyl-2,6,6-trimethylcyclohex-3-enyl ketone and is use in creating perfumes and scents in such items as perfumes, colognes, toilet water and personal care products.
Abstract: A process for the production of an intermediate mixture of &bgr;-isophorone epoxide and its isomer 4-hydroxyisophorone (HIP), comprising reacting &bgr;-isophorone with an organic percarboxylic acid, in the form of its non-aqueous solution, in an inert solvent.
Type:
Grant
Filed:
February 28, 2002
Date of Patent:
October 22, 2002
Assignee:
Degussa AG
Inventors:
Steffen Krill, Klaus Huthmacher, Sylvain Perrin
Abstract: One aspect of the present invention relates to methods for the transition-metal-catalyzed asymmetric 1,4-addition of a nucleophile, e.g., hydride, to cyclic and acyclic enoates and enones. In certain embodiments of the methods of the present invention, the transition metal catalyst consists essentially of copper and an asymmetric bidentate bisphosphine ligand.
Type:
Grant
Filed:
September 13, 2000
Date of Patent:
October 15, 2002
Assignee:
Massachusetts Institute of Technology
Inventors:
Stephen L Buchwald, Daniel H. Appella, Yasunori Moritani, Ryo Shintani, Valdas Jurkauskas
Abstract: A process for preparing aldols by catalytic reaction of aldehydes and/or ketones comprises conducting said reaction in the channels of a microstructured reaction system.
Abstract: Preparation of cyclic, &agr;,&bgr;-unsaturated ketones of formula II by dehydrogenation of cyclic ketones which conform to formula I
in which n denotes an integer from 1 to 10, and which may be substituted, at elevated temperature in the presence of catalysts in the vapor phase, wherein the reaction is carried out in the absence of oxygen or in the presence of less than 0.5 mol of oxygen per mol of compound I at temperatures ranging from 250° to 600° C. and using catalysts having a surface area (BET) of more than 0.5 m2/g.
Abstract: &agr;,&bgr;-Unsaturated keto compounds are prepared by base-catalyzed aldol condensation of aldehydes and/or ketones having from 1 to 15 carbon atoms, comprising:
reacting the aldehydes and/or ketones with an aqueous catalyst solution under adiabatic reaction conditions; and
separating the reaction mixture obtained by rapid distillation into a top product comprising water, aldehyde and/or ketone and a bottom product comprising &agr;,&bgr;-unsaturated keto compounds and aqueous catalyst phase.
Abstract: Process for the production of 2,2,6-trimethylcyclohexane-1,4-dione by epoxidation of &bgr;-isophorone with organic percarboxylic acids at a water content below 5 wt.-% and subsequent isomerization of the mixture of &bgr;-isophorone epoxide and hydroxyisophorone.
Type:
Grant
Filed:
May 8, 2001
Date of Patent:
July 16, 2002
Assignee:
Degussa AG
Inventors:
Steffen Krill, Klaus Huthmacher, Sylvain Perrin
Abstract: A method for continuously producing a ketone in a tube reactor at elevated weight hourly space velocities and in the presence of a catalyst from feed material comprised of a first carboxylic acid or aldehyde or their derivatives and a second carboxylic acid and a method for using the ketone production method to produce herbicidal or other agricultural compounds.
Abstract: Lower alkyl- and lower alkylidene-substituted, saturated or unsaturated cyclohexadecanones are grand fragrances with muscone note with which perfumes with new odor notes can be prepared.
Abstract: Disclosed is a process for oxidizing organic compounds using hydrogen peroxide to oxidize an oxidizable organic substrate in the presence of a silylated peroxide-activating metal/silica-containing catalyst and to a method of preparing such a catalyst.
Abstract: Process for the continuous preparation of &agr;- and/or &bgr;-ionone or homologous compounds using concentrated sulfuric acid at temperatures from 20 to 90° C.
Abstract: The invention relates to an improved process for preparing [(3aR,4S,7aS)4-bromooctahydro-7a-methyl-1H-indene-1,5-dione]. (S)-(+)-2,3,7,7a-tetrahydro-7a-methyl-1H-indene-1,5(6H)-dione is reduced by reaction with diisobutylaluminum hydride and hexamethylphosphoric triaminde in the presence of a catalyst of the formula R—Cu, wherein R is
and R1, R2 and R3 are each, independently, selected from the group consisting of C1-7 alkyl, phenyl, phenyl substituted by at least one C1-4 alkyl group, benzyl, or benzyl substituted by at at least one C1-4 alkyl group to form a reductate. The reductate is then treated with a bromine-containing electrophile to yield (3aR,4S,7aS)4-bromooctahydro-7a-methyl-1H-indene-1,5-dione.
Abstract: The invention relates to bicyclic aldehydes and ketones of formula (I):
wherein
n is 1 or 2;
R1 and R4 are independently H or CH3; and
R2 and R3 are independently H, CH3 or CH2CH3
The invention also provides odorant compositions containing at least one compound of formula (I). A process for the manufacture of R1-methyl substituted compounds of formula (I) having a bridgehead-positioned double bond, as well as intermediates thereof is also provided.
Abstract: The invention relates to a novel process for the preparation of hydroxyalkyl- and acyloxyalkyl-substituted cycloketones by free-radical addition of hydroxyalkenes and acyloxyalkenes respectively to cyclic ketones.
Type:
Grant
Filed:
December 18, 1998
Date of Patent:
April 24, 2001
Assignee:
Haarmann & Reimer GmbH
Inventors:
Alfred Krempel, Oskar Koch, Harry Erfurt
Abstract: The invention relates to a process for the halogenation of cyclopropylmethyl ketone with at least one dihalo-triorganophosphorane of the general formula I
R3PHal2 (I),
in which the radicals R can be the same or different and denote a saturated or unsaturated aliphatic C1-C20 hydrocarbon radical, a phenyl or (C1-C4 alkyl)phenyl radical, which may be optionally substituted by one or two fluorine, chlorine and/or nitro groups, P stands for phosphorus and Hal denotes chlorine, bromine, or iodine, at a temperature of from 800° to 130° C.
Type:
Grant
Filed:
September 1, 1999
Date of Patent:
March 27, 2001
Assignee:
BASF Aktiengesellschaft
Inventors:
Michael Henningsen, Armin Stamm, Martin Fischer, Wolfgang Siegel
Abstract: Novel macrocyclic diene ketone compounds useful as fragrance materials are described having the following general formula (I):
where R1, R2, R3 and R4 are each either a hydrogen atom or a C1 to C4 alkyl, a is the integer 1 or 2 and b is an integer in a range from 1 to 6. Novel pathways are described for synthesizing these macrocyclic diene ketones, as well as saturated and mono-unsaturated macrocyclic ketones having the following general formula (IV):
where R1, R2, R3 and R4 are each independently a hydrogen atom or a C1 to C4 alkyl, a is the integer 1 or 2 and b is an integer in a range from 1 to 6.
Type:
Grant
Filed:
May 21, 1999
Date of Patent:
March 13, 2001
Assignees:
Takasago International Corporation, Takasago Institute for Interdisciplinary Science, Inc.
Inventors:
Andrew T. Lupo, Jr., Tetsuo Nakatsu, John Caldwell, Michael E. Lankin, Carter B. Green, Takashi Aida
Abstract: A process for the manufacture of a symmetrical, terminally ring-substituted polyenes by reacting a polyene di(O,O-dialkyl acetal) with a cyclic dienol ether in the presence of a Lewis or Brönsted acid, hydrolyzing the condensation product resulting therefrom and cleaving off alcohol under basic or acidic conditions from the polyene derivative produced at this stage. The novel cyclic dienol ethers, as well as, novel intermediates resulting from the condensation and additional intermediates in this process form further aspects of the invention. The final products are primarily carotenoids, which find corresponding use, e.g., as colorings and pigments for foodstuffs, animal products, etc.
Abstract: A process for the manufacture of trans-(R,R)-actinol by diasteroselective transfer hydrogenation of levodione comprises hydrogenating (R)-levodione in the presence of a hydrogen donor, which simultaneously can be used as the solvent, and an amino-amide-ruthenium complex, especially of the formula RuH(L{—H})(Y), wherein Y signifies a neutral ligand and L signifies an optionally optically active monosulphonylated diamine ligand, as defined in more detail in the description. Moreover, the invention is concerned with some of the amino-amide-ruthenium complexes and with the corresponding precursors to these complexes, which have halogen in place of H. The product of the process in accordance with the invention, trans-(R,R)-actinol, is known as an important building block for the synthesis of carotenoids, e.g. zeaxanthin. By the process trans-(R,R)-actinol is made available in particularly high enantiomeric and diasteromeric purity.
Type:
Grant
Filed:
October 20, 1998
Date of Patent:
February 13, 2001
Assignee:
Roche Vitamins Inc.
Inventors:
Yvo Crameri, Kurt Püntener, Michelangelo Scalone
Abstract: Disclosed is a process for producing 5-cyclohexadecen-1-one continuously from 1,2-divinylcyclododecanol in a short time in an efficient manner without side reactions. In the process, 1,2-divinylcyclododecanol as a starting material is supplied from a raw material container 1 by a dosage pump 2 to a flash unit 3 which is set under a vacuum of 5 mm Hg or less by a vacuum pump 8 and is heated. 1,2-Divinylcyclododecanol which is flashed in the flash unit is supplied to a reactor 4 which is heated to 400 to 650° C. and is set under a vacuum of 5 mm Hg or less whereby 1,2-divinylcyclododecanol is converted into 5-cyclohexadecen-1-one. The reaction product is discharged from the top of the reactor and is cooled to recover the objective 5-cyclohexadecen-1-one in the recovery container 6. The reduction in the pressure of the apparatus is preferably performed by a vacuum pump 8 via a hydrochloric acid trap 7 comprising, for example, sodium methylate/methanol cooled to −78 to −100° C.
Abstract: Acid catalyzed cyclization of Diels-Alder adducts of myrcene is performed in the presence of hydroxyl-containing compounds, giving the resulting mixtures of isomeric acyloctahydronaphthalenes enhanced quantities of isomers that are particularly useful in perfumery because of their woody-amber odors with enhanced amber note.
Type:
Grant
Filed:
August 19, 1998
Date of Patent:
December 12, 2000
Assignee:
Millennium Specialty Chemicals
Inventors:
Mark B. Erman, Carlos G. Cardenas, Henri M. Hoffmann
Abstract: A widely applicable process for the manufacture of carotenoids by a Wittig reaction comprises carrying out the Wittig reaction in a polar reaction medium in a manner such that neither the reactants nor the thus-manufactured carotenoid are significantly dissolved in the reaction medium. An especially suitable reaction medium is a polar, toxicologically harmless solvent which remains monophasic on the addition of water in an amount up to about 30 vol. % and which permits the triarylphosphine oxide which is formed to dissolve well. Lower alcohols and acetone, as sole solvents or as mixtures with one another and/or with water, are especially suitable as the polar reaction medium. This process permits the use of much more concentrated reaction mixtures, simplifies the regeneration of the solvent and generally the reaction procedure, and avoids toxicologically objectionable solvents such as halogenated hydrocarbons.
Type:
Grant
Filed:
September 4, 1998
Date of Patent:
November 21, 2000
Assignee:
Roche Vitamins Inc.
Inventors:
Paul Kreienbuhl, Peter Rudin, Werner Rudolph
Abstract: Process for the continuous preparation of .alpha.- and/or .beta.-ionone or homologous compounds using concentrated sulfuric acid at temperatures from 20 to 90.degree. C.
Abstract: A process carried out in a reaction column for the chemical reaction of substances the reaction of which is affected by an unfavorable equilibrium position of the main reaction or a preceding equilibrium, wherein during the reaction one or more substances to be separated are continuously removed from the reaction mixture by one or more auxiliaries.
Type:
Grant
Filed:
May 4, 1998
Date of Patent:
May 30, 2000
Assignee:
RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
Abstract: Described are trimethylcyclohexenylcyclopropyl ketones having the structure: ##STR1## wherein one of the dashed lines is a carbon--carbon double bond and the other of the dashed lines is a carbon--carbon single bond, uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles, and mixtures of same with 3-methyl-1-phenylpentanol-5 and/or butanoylcyclohexane derivatives and/or acetic or propionic acid esters of o-methylphenyl isopropanol.
Abstract: The present invention relates to a process for preparing 2-cyclo-alkenones of the formula I ##STR1## which comprises subjecting a 2-alkoxycycloalkanone and/or a 2-hydroxyalkanone ketal, in which n is an integer from 0 to 20, m is 0, 1, 2 or 3 and R is alkyl, alkylaryl, aryl, arylalkyl, alkenyl or alkynyl, to an elimination reaction in the gas phase on an acidic heterogeneous catalyst.
Type:
Grant
Filed:
February 1, 1999
Date of Patent:
January 4, 2000
Assignee:
BASF Aktiengesellschaft
Inventors:
Matthias Eiermann, Klaus Ebel, Jorg Botzem
Abstract: The invention disclosed relates to a new class of abscisic acid (ABA) analogs of formula I ##STR1## wherein one of R.sub.1 is alkenyl, alkynyl, aryl, cycloalkenyl, other farther substituted carbon chain including deuterium containing residues, and carbon containing substituents with heteroatoms and halogens and the other is methyl, and wherein the five member carbon side chain includes a methyl group at C3, with C5 attached to the ring as shown, including a trans double bond at the C4-C5 position, or a triple bond at this position, and either a cis or a trans double bond at the C2-C3 position, and R.sub.2 is CH.sub.2 OH, CHO, COOH, COO alkyl, or derivatives thereof, and wherein the cyclohexanone ring double bond may also be reduced and to a novel process for synthesizing such ABA analogs.
Type:
Grant
Filed:
September 22, 1998
Date of Patent:
December 21, 1999
Assignee:
National Research Council of Canada
Inventors:
Suzanne R. Abrams, John J. Balsevich, Adrian J. Cutler, Bo Lei, Patricia A. Rose
Abstract: Cyclopropyl alkyl ketones are separated from 3-acyltetrahydrofuran-2-ones by adding an alcohol, water or a water/alcohol mixture to a reaction product containing C.sub.1-4 -alkyl cyclopropyl ketone and 4,5-dihydro-2-alkylfuran by-product and an acid catalyst and reacting the by-product with the added alcohol, water of water/alcohol mixture before, during or after distilling said reaction product; and effectively separating C.sub.1 -.sub.4 -alkyl cyclopropyl ketone from reaction by-products.In the preparation of cyclopropyl alkyl ketones from 3-acyltetrahydrofuran-2-ones very reactive 4,5-dihydro-2-alkylfurans are also produced. By reacting such compounds with nucleophilic compounds, such as alcohols or water, before, during or after distillation of the reaction products, it is possible reliably to separate off the 4,5-dihydro-2-alkylfurans as high-boiling addition compounds.
Type:
Grant
Filed:
March 8, 1999
Date of Patent:
December 14, 1999
Assignee:
Huels Aktiengesellschaft
Inventors:
Manfred Kaufhold, Wolfgang Kleemiss, Udo Jegelka, Michael Korell
Abstract: The invention relates to the use of the known compound 2,6-dichloro-3-fluoro-benzonitrile as active compound in selectively-herbicidal compositions, and to new preparation processes and new intermediates for the preparation of this compound.
Type:
Grant
Filed:
July 28, 1997
Date of Patent:
October 20, 1998
Assignee:
Bayer Aktiengesellschaft
Inventors:
Reinhard Lantzsch, Werner Bussmann, Josef Kasbauer, Markus Dollinger, Hans-Joachim Santel
Abstract: The invention relates to a novel process for simultaneously preparing cyclopropyl alkyl ketones and 4,5-dihydroalkylfurans from 3-acyltetrahydrofuran-2-ones in the presence of a metal salt according to the scheme ##STR1## during the reaction, high-boiling poly (ethylene glycol) dialkyl ethers are then used. By introducing the solvent, the metal salt and the 3-acyltetrahydrofuran-2-one in a molar excess to the metal salt, heating the mixture to 160.degree. to 220.degree. C. and adding further 3-acyltetrahydrofuran-2-one, the desired products are obtained in high yields. The metal salt can, moreover, be recovered in a simple manner by washing with water.
Abstract: The invention is concerned with novel odorants, including the compounds of the formula ##STR1## wherein R.sup.1 .dbd.R.sup.4 .dbd.CH.sub.3 and R.sup.2 .dbd.R.sup.3 .dbd.H orR.sup.1 .dbd.R.sup.2 .dbd.R.sup.3 .dbd.H and R.sup.4 .dbd.CH.sub.3, orR.sup.1 +R.sup.2 .dbd.--CH.sub.2 CH.sub.2 -- and R.sup.3 .dbd.H and R.sup.4 .dbd.CH.sub.3, orR.sup.1 .dbd.R.sup.4 .dbd.CH.sub.3 and R.sup.2 +R.sup.3 .dbd.--CH.sub.2 -- orR.sup.1 .dbd.CH.sub.3 and R.sup.2 .dbd.R.sup.3 .dbd.H and R.sup.4 .dbd.CH.sub.2 CH.sub.3 orR.sup.1 .dbd.R.sup.2 .dbd.R.sup.4 .dbd.CH.sub.3 and R.sup.3 .dbd.H and R.sup.5 .dbd.H (preferred) or CH.sub.3.
Type:
Grant
Filed:
April 25, 1996
Date of Patent:
January 13, 1998
Assignee:
Givaudan-Roure (International) SA
Inventors:
Jerzy A. Bajgrowicz, Alain Bringhen, Georg Frater, Urs Muller
Abstract: Improved process for the preparation of astaxanthin by Wittig reaction of 2 mol of 3-methyl-5-(2,6,6-trimethyl-3-oxo-4-hydroxy-1-cyclohexenyl)-2,4-pentadieny ltriarylphosphonium salts with one mol of 2,7-dimethyl-2,4,6-octatrienedial avoiding the use of halohydrocarbons as solvents.
Type:
Grant
Filed:
March 15, 1996
Date of Patent:
August 5, 1997
Assignee:
BASF Aktiengesellschaft
Inventors:
Wolfgang Krause, Klaus Henrich, Joachim Paust, Hansgeorg Ernst
Abstract: The invention relates to a novel process for the simultaneous preparation of cyclopropyl alkyl ketones and 4,5-dihydroalkylfurans from 3-acyltetrahydrofuran-2-ones using a metal salt according to the diagram ##STR1## In the reaction, N-alkyllactams and/or N-acylmorpholines which are high-boiling and only slightly miscible with water are used. By charging the solvent, the metal salt and the 3-acyltetrahydrofuran-2-one in a molar excess with respect to the metal salt, heating the mixture to 160.degree. to 220.degree. C. and metering in further 3-acyl-tetrahydrofuran-2-one, the desired products are obtained in high yields. The metal salt can moreover be recovered in a simple manner by washing with water.
Abstract: Abstract of the Disclosure: Compounds of the formula I ##STR1## where R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, R.sup.2 is C.sub.1 -C.sub.4 -alkyl and R.sup.3 is an ether, silyl ether or acetal protective group which can be converted into a hydroxyl group by hydrolysis, in particular one of the radicals ##STR2## and a process for preparing these compounds by reacting an alkenyne of the formula II ##STR3## in an inert solvent in the presence of lithium amide with a cyclohexenone of the formula III ##STR4## and the use of the compounds of the formula I for preparing astaxanthin, are described.
Type:
Grant
Filed:
May 23, 1995
Date of Patent:
April 29, 1997
Inventors:
Hansgeorg Ernst, Walter Dobler, Joachim Paust, Udo Rheude
Abstract: A process is disclosed for the removal of the 4-protected hydroxy group from compounds of the following formula: ##STR1## where A is --COOAlkyl and B is hydroxy, or A and B together represent either oxo or .dbd.CHCOOAlkyl, where X.sup.1 and X.sup.2 are the same or different and represent hydrogen or a hydroxy-protecting group, and where X.sup.3 is ##STR2## with a hydrogen radical source, such as tributyltin hydride or tris(trimethylsilyl)silane, and a radical initiator, such as AIBN or irradiation.
Type:
Grant
Filed:
May 16, 1995
Date of Patent:
October 8, 1996
Assignee:
Wisconsin Alumni Research Foundation
Inventors:
Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson