Abstract: The present invention relates to [1] a method of producing 1-(2-t-butylcyclohexyloxy)-2-butanol including a step of hydrogenating 1-(2-t-butylphenyloxy)-2-butanol under a condition at a hydrogen pressure of from 1 to 5 MPa in the presence of a palladium catalyst (A) supported on peat-derived active carbon and a metal catalyst (B) containing one or more kinds of members selected from ruthenium, rhodium, platinum, and nickel; and [2] a perfume composition containing 1-(2-t-butylcyclohexyloxy)-2-butanol obtained by the foregoing method. According to the present invention, 1-(2-t-butylcyclohexyloxy)-2-butanol having a woody or amber-like fragrance as a perfume material and excellent fragrance notes can be obtained in a high purity because of a small remaining amount of a reaction intermediate and in a high yield.

Abstract: The present invention relates to [1] a method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol including a step of adjusting a raw material mixture containing a 1-(2-t-butylphenyloxy)-2-alkanol represented by the formula (1) to a pH of from 7.5 to 10.0 and hydrogenating it in the presence of a palladium catalyst (A) and a metal catalyst (B) containing one or more kinds of members selected from ruthenium, rhodium, platinum, and nickel; and [2] a perfume composition containing a 1-(2-t-butylcyclohexyloxy)-2-alkanol obtained by the foregoing method. The present invention provides a method of efficiently producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol having a high trans-isomer content and a strong woody or amber-like fragrance as a perfume material and also having excellent persistence of aroma. (In the formula, R1 is a methyl group or an ethyl group.

Abstract: The present invention relates to [1] a method of producing 1-(2-t-butylcyclohexyloxy)-2-butanol including a step of hydrogenating 1-(2-t-butylphenyloxy)-2-butanol under a condition at a hydrogen pressure of from 1 to 5 MPa in the presence of a palladium catalyst (A) supported on peat-derived active carbon and a metal catalyst (B) containing one or more kinds of members selected from ruthenium, rhodium, platinum, and nickel; and [2] a perfume composition containing 1-(2-t-butylcyclohexyloxy)-2-butanol obtained by the foregoing method. According to the present invention, 1-(2-t-butylcyclohexyloxy)-2-butanol having a woody or amber-like fragrance as a perfume material and excellent fragrance notes can be obtained in a high purity because of a small remaining amount of a reaction intermediate and in a high yield.

Abstract: The present invention relates to [1] a method of producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol including a step of adjusting a raw material mixture containing a 1-(2-t-butylphenyloxy)-2-alkanol represented by the formula (1) to a pH of from 7.5 to 10.0 and hydrogenating it in the presence of a palladium catalyst (A) and a metal catalyst (B) containing one or more kinds of members selected from ruthenium, rhodium, platinum, and nickel; and [2] a perfume composition containing a 1-(2-t-butylcyclohexyloxy)-2-alkanol obtained by the foregoing method. The present invention provides a method of efficiently producing a 1-(2-t-butylcyclohexyloxy)-2-alkanol having a high trans-isomer content and a strong woody or amber-like fragrance as a perfume material and also having excellent persistence of aroma. (In the formula, R1 is a methyl group or an ethyl group.

Abstract: Disclosed is a method for producing an alicyclic alcohol represented by general formula (III) which is useful as a starting material for a flavor mixture or the like at low cost in high yield. The alicyclic alcohol represented by general formula (III) is produced by preparing a cyclohexanecarbonyl compound represented by general formula (II) through the carbonylation of an unsaturated hydrocarbon represented by general formula (I) (preferably a compound obtained through the partial reduction of a diene compound) using carbon monoxide in the presence of HF, and thereafter reducing the cyclohexanecarbonyl compound. In formulae (I), (II), and (III), R1 represents an alkyl group having 1 to 4 carbon atoms, R2 represents an alkyl group having 1 to 4 carbon atoms, R3 represents an OH group, fluorine, or an OR4 group, and R4 represents an alkyl group having 1 to 4 carbon atoms.

Abstract: The present invention relates to a perfume composition as a raw material of fruity perfumes which has a conventionally unknown peculiar fresh, woody, floral, grassy-leafy nuance and is capable of harmonizing with various perfumes to provide perfume preparations having a more sophisticated odor or scent. The perfume composition of the present invention includes a compound represented by the general formula (I): wherein R1 and R2 are each independently a hydrocarbon group having 1 to 4 carbon atoms; and R3 is a hydrocarbon group having 2 to 4 carbon atoms.

Abstract: Disclosed is a method for producing an alicyclic alcohol represented by general formula (III) which is useful as a starting material for a flavor mixture or the like at low cost in high yield. The alicyclic alcohol represented by general formula (III) is produced by preparing a cyclohexanecarbonyl compound represented by general formula (II) through the carbonylation of an unsaturated hydrocarbon represented by general formula (I) (preferably a compound obtained through the partial reduction of a diene compound) using carbon monoxide in the presence of HF, and thereafter reducing the cyclohexanecarbonyl compound. In formulae (I), (II), and (III), R1 represents an alkyl group having 1 to 4 carbon atoms, R2 represents an alkyl group having 1 to 4 carbon atoms, R3 represents an OH group, fluorine, or an OR4 group, and R4 represents an alkyl group having 1 to 4 carbon atoms.

Abstract: The present invention relates to a perfume composition as a raw material of fruity perfumes which has a conventionally unknown peculiar fresh, woody, floral, grassy-leafy nuance and is capable of harmonizing with various perfumes to provide perfume preparations having a more sophisticated odor or scent. The perfume composition of the present invention includes a compound represented by the general formula (I): wherein R1 and R2 are each independently a hydrocarbon group having 1 to 4 carbon atoms; and R3 is a hydrocarbon group having 2 to 4 carbon atoms.

Abstract: The present invention relates to alcohol compounds having a scent of natural lily of the valley substantially without any woody scent limiting their applications to raw materials of perfume preparations, and a process for producing the alcohol compounds. The alcohol compounds are represented by the following general formula (I): wherein R1 is a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; and any one of dotted lines represents a double bond, and the remaining three dotted lines each represent a single bond.

Abstract: The present invention relates to alcohol compounds having a scent of natural lily of the valley substantially without any woody scent limiting their applications to raw materials of perfume preparations, and a process for producing the alcohol compounds. The alcohol compounds are represented by the following general formula (I): wherein R1 is a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; and any one of dotted lines represents a double bond, and the remaining three dotted lines each represent a single bond.

Abstract: A process for preparing an orange oil comprising the steps of mixing a raw material oil containing valencene with a high-boiling solvent having a boiling point exceeding 240° C. under normal pressure, to give a mixture, and fractionally distilling the mixture obtained, optionally comprising the step of subjecting to an alkali treatment the raw material oil before fractional distillation or a distillate fraction obtained after fractional distillation; and an orange oil obtained by the process as defined above.

Abstract: There is provided a noble process for producing a salicylic ester for perfumes which comprises the step of transesterifying a salicylic lower alkyl ester with an alcohol having at least one carbon atom which is located adjacent to a hydroxyl-bonded carbon atom and has one or more hydrogen atoms bonded thereto, in the presence of a tin-based catalyst. The process of the present invention enables the salicylic ester to be produced at a high yield and is free from handling problems such as precipitation of solids in a distillation residue obtained after the reaction, and the catalyst used therein is reusable.

Abstract: A process for preparing an orange oil comprising the steps of mixing a raw material oil containing valencene with a high-boiling solvent having a boiling point exceeding 240° C. under normal pressure, to give a mixture, and fractionally distilling the mixture obtained, optionally comprising the step of subjecting to an alkali treatment the raw material oil before fractional distillation or a distillate fraction obtained after fractional distillation; and an orange oil obtained by the process as defined above.

Abstract: The invention discloses a method for the production of a macrocyclic lactone represented by a formula (2), which comprises subjecting a hydroxycarboxylic acid ester represented by a formula (1) to intramolecular esterification reaction. In the formulae (1) and (2), m is an integer of from 5 to 10, n is an integer wherein m+n becomes from 11 to 16, X represents —CH2—, —CH═CH—, —O—, —S— or —NH—, and R represents a hydrocarbon group having from (m+n+2) to 40 carbon atoms or a group represented by —(AO)pR1 wherein AO represents an alkyleneoxy group having from 2 to 4 carbon atoms, p is average addition mole number of alkylene oxide and R1 represents a hydrocarbon group having a specified number of carbon atoms so that the total number of carbon atoms of the —(AO)pR1 group becomes from (m+n+2) to 40.

Abstract: The present invention provides a process for producing hydroxycarboxylic acid esters easily, further at a high reaction selectivity, by using an inexpensive catalyst. That is, the present invention provides a process for producing hydroxycarboxylic acid esters, which comprises hydrogenating dicarboxylic acid diesters having 3 to 20 carbon atoms in the dicarboxylic acid moiety in the presence of a copper catalyst comprising 1 to 40% by weight of copper as copper oxides.

Abstract: The present invention provides a process for producing hydroxycarboxylic acid esters easily, further at a high reaction selectivity, by using an inexpensive catalyst. That is, the present invention provides a process for producing hydroxycarboxylic acid esters, which comprises hydrogenating dicarboxylic acid diesters having 3 to 20 carbon atoms in the dicarboxylic acid moiety in the presence of a copper catalyst comprising 1 to 40% by weight of copper as copper oxides.

Abstract: The object of the present invention resides in efficiently providing unsaturated alcohol from an .alpha.,.beta.-unsaturated aldehyde.The present invention provides a process for preparing unsaturated alcohol by selectively reducing the aldehyde group of an .alpha.,.beta.-unsaturated aldehyde in the presence of a primary or a secondary alcohol having 2 to 8 carbon atoms using an aluminum alcoholate to produce an unsaturated alcohol such as compounds represented by the formula (III). ##STR1## (wherein R represents an alkyl group having 1 to 3 carbon atoms) wherein the reaction is carried out with addition of a protonic acid.