Takasago International Corporation

Hironori Maeda

Yoji Hori

Shinya Yamada

Hideo Shimizu

Kenya Ishida

Kazushi Mashima

Hisanori Itoh

Takashi Ohshima

Kiyoto Hori

Takanori Iwasaki

The present invention relates to: a method for converting a hydroxyl group of an alcohol; and a catalyst which makes the method possible. A method for converting a hydroxyl group of an alcohol according to the present invention is characterized by producing a compound represented by CH(R)(R)Nu (wherein R, Rand Nu are as defined below) by reacting an alcohol represented by CH(R)(R)OH (wherein each of Rand Rrepresents a hydrogen atom, an optionally substituted alkyl group, or the like) and a compound having an active proton, which is represented by H-Nu (wherein Nu represents a group represented by &#x2014;CHX-EWGor &#x2014;NRR; Xrepresents a hydrogen atom or the like; EWGrepresents an electron-withdrawing group; and each of Rand Rrepresents a hydrogen atom, an optionally substituted alkyl group, or the like), with each other in the presence of a complex of a group 7-11 metal of the periodic table and at least one solid base that is selected from the group consisting of layered double hydroxides, composite oxides and calcium hydroxide.

Method for converting hydroxyl group of alcohol

The present invention relates to a method for producing a 3-methylcycloalkenone compound and a method for producing muscone. In the presence of a zirconium oxide catalyst, a diketone represented by the following general formula (1): wherein in formula (1), n represents 8, 9, 10, 11 or 12,is subjected to a vapor-phase intramolecular condensation reaction, whereby a 3-methylcycloalkenone compound can be produced with high reaction efficiency. When a 3-methylcyclopentadecenone compound produced by this method is hydrogenated in a known manner, muscone can be produced efficiently.

Method for producing 3-methylcycloalkenone compound

An object of the present invention is to provide a method for manufacturing an optically active menthol having fewer steps, which generates less environmentally polluting waste because a catalytic reaction is involved in all of the steps, and is capable of saving a production cost. The present invention relates to a method for manufacturing an optically active menthol, including the following steps: A-1) asymmetrically hydrogenating at least one of geranial and neral to thereby obtain an optically active citronellal, B-1) conducting a ring-closure reaction of the optically active citronellal in the presence of an acid catalyst to thereby obtain an optically active isopulegol, and C-1) hydrogenating the optically active isopulegol to thereby obtain an optically active menthol.

Method for manufacturing optically active menthol

The present invention provides a catalyst used for manufacturing an optically active carbonyl compound by selective asymmetric hydrogenation of an &#x3b1;, &#x3b2;-unsaturated carbonyl compound, which is insoluble in a reaction mixture, and a method for manufacturing the corresponding optically active carbonyl compound. Particularly, the invention provides a catalyst for obtaining an optically active citronellal useful as a flavor or fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. The invention relates to a catalyst for asymmetric hydrogenation of an &#x3b1;, &#x3b2;-unsaturated carbonyl compound, which comprises: a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which the at least one metal is supported on a support; an optically active cyclic nitrogen-containing compound; and an acid, and also relates to a method for manufacturing an optically active carbonyl compound using the same.

Catalyst for asymmetric hydrogenation and method for manufacturing optically active carbonyl compound using the same

The present invention provides a catalyst used for manufacturing an optically active carbonyl compound by selective asymmetric hydrogenation of an &#x3b1;,&#x3b2;-unsaturated carbonyl compound, which is insoluble in a reaction mixture, and a method for manufacturing the corresponding optically active carbonyl compound. Particularly, the invention provides a catalyst for obtaining an optically active citronellal useful as a flavor or fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. The invention relates to a catalyst for asymmetric hydrogenation of an &#x3b1;,&#x3b2;-unsaturated carbonyl compound, which comprises: a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which the at least one metal is supported on a support; an optically active peptide compound; and an acid, and also relates to a method for manufacturing an optically active carbonyl compound using the same.

This invention aims at providing a catalyst for producing an optically active aldehyde or an optically active ketone, which is an optically active carbonyl compound, by carrying out selective asymmetric hydrogenation of an &#x3b1;,&#x3b2;-unsaturated carbonyl compound, particularly a catalyst which is insoluble in a reaction mixture for obtaining optically active citronellal which is useful as a flavor or fragrance, by carrying out selective asymmetric hydrogenation of citral, geranial or neral; and a method for producing a corresponding optically active carbonyl compound. The invention relates to a catalyst for asymmetric hydrogenation of an &#x3b1;,&#x3b2;-unsaturated carbonyl compound, which comprises a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table is supported on a support, an optically active cyclic nitrogen-containing compound and an acid.

Catalyst for asymmetric hydrogenation

The invention relates to a method for producing an azoline compound represented by the general formula (3): wherein Rrepresents an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, a halogen atom, a substituted amino group, a substituted carbamoyl group or an optionally substituted heterocyclic group; R, R, Rand Rmay be the same or different and each represents a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, a halogen atom, a substituted amino group, a substituted carbamoyl group or an optionally substituted heterocyclic group; two arbitrary groups selected from R, R, Rand Rmay bond to each other to form a ring; and Zrepresents an oxygen atom, a sulfur atom or a selenium atom;comprising reacting a carboxylic acid or a carboxylic acid derivative represented by the general formula (1):RCOR&#x2003;&#x2003;(1)wherein Ris as defined above; Rrepresents a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aryl group; and Rand Rmay bond to each other to form a ring;with an aminochalcogenide represented by the general formula (2): wherein R, R, R, Rand Zare as defined above;in the presence of a compound containing a group 12 metal element in the periodic table.

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Kanagawa, Japan

Hironori Maeda