Kao Corporation

Takashi Aoki

Takahiro Hirose

Shoichi Tahara

Junji Koshino

Shinji Kotachi

Kenji Tanino

Tomotaka Matsumoto

Yoshiharu Ataka

Taku Mimura

Tsuyoshi Toyabe

Yuki Nakazawa

Herwick Tan

Natacha Jerome

The present invention relates to a method for producing a 1,3-dioxan-5-one by a short-step and simple method from raw materials that are procurable easily and inexpensively, using, as a raw material, a 1,3-dioxane that is a mixture containing a 1,3-dioxolane. Provided is a method for producing a 1,3-dioxan-5-one, including using a mixture of a compound represented by the following formula (I) and a compound represented by the following formula (II) as a raw material, the method including a step of oxidizing the mixture under an oxidative esterification condition (step 2): wherein, in the formulae (I) and (II), Rand Reach independently represent a hydrogen atom or a monovalent hydrocarbon group, or Rand Rare bonded to each other to form a divalent hydrocarbon group for constituting a ring structure.

Method for manufacturing 1,3-dioxane-5-one

The present invention is to provide a method of producing a glyceric acid ester which is easy for production and high in yield, and in which a pyridine to be used for the reaction is easily reused. Provided is a method of producing a compound represented by the following formula (II), including a step of oxidatively esterifying Compound A represented by the following formula (I) with Compound B selected from an organic nitroxyl radical, an N-hydroxy form thereof, and a salt containing an oxo ammonium cation of them, and an oxidizing agent in the presence of a pyridine having an alkyl substituent, wherein the use amount of Compound B is 0.0001 or more and 0.1 or less in terms of a molar ratio relative to Compound A: wherein, in the formulae (I) and (II), Rand Reach independently represent a hydrogen atom or a monovalent hydrocarbon group, or Rand Rare bonded to each other to form a divalent hydrocarbon group for constituting a ring structure.

Method for producing glyceric acid ester

The present invention relates to providing a novel glyceric acid ester which can be produced in a high yield and is expected to be applied as a synthetic intermediate, and a method of producing the same. In addition, the present invention relates to providing a novel glyceric acid ester which exhibits a high recovery in a water-washing step after the reaction and a small work load at the time of production, and is expected to be applied as a synthetic intermediate, and a method of producing the same. The present invention provides a method of producing a compound represented by the following formula (II), including a step of oxidatively esterifying a compound represented by the following formula (I): wherein, in the formulae (I) and (II), Rand Reach independently represent a hydrogen atom or a monovalent hydrocarbon group, or Rand Rare bonded to each other to form a divalent hydrocarbon group for constituting a ring structure, provided that the case where Rand Rare a methyl group at the same time is excluded.

Provided are: a method for producing N,N-dialkylhomofarnesic acid amide, which is a precursor of (&#xb1;)-3a,6,6,9a-tetramethyldodecahydronaphtho[2.1-b]furan that is useful as a fragrance, at a high recovery rate of a raw material, at a high purity and at a high yield; and a method for producing (&#xb1;)-3a,6,6,9a-tetramethyldodecahydronaphtho[2.1-b]furan. It is a method for producing N,N-dialkylhomofarnesic acid amide, said method including reacting nerolidol with N,N-dialkylformamide dimethyl acetal under the conditions that the N,N-dialkylformamide dimethyl acetal can be refluxed, wherein the molar ratio of the N,N-dialkylformamide dimethyl acetal to the nerolidol is in a range of 1.5 to 3.

Method for producing N,N-dialkylhomofarnesic acid amide

The present invention provides a method of using, as a fragrance component, a compound that is excellent in fragrance retention and that has green floral and fruity like odors, which are useful as fragrances, and a fragrance composition with sweetness and voluminousness containing the compound. The present invention relates to a fragrance composition containing 2-n-pentyl cyclopentanone oxime and a method of using 2-n-pentyl cyclopentanone oxime as a fragrance component.

Fragrance composition

Provided are a compound and a fragrance composition containing the same, wherein the compound has a spicy tone that is useful as a fragrance, particularly a cumin-like odor, it is stable in an aqueous vehicle, and it emphasizes spicy-, green-, floral-, woody-, and citrus-like various odors by being blended with other fragrances, which allows oil-, chemical-, and metallic-like undesirable odors to be suppressed. A nitrile compound represented by Formula (I-3), Formula (I-2), or Formula (I-1). 

Nitrile compound

It is intended to provide a compound and a fragrance composition containing the same, wherein the compound has an odor with a tone of musk and a side note of woody tone, which are useful as fragrances, is excellent in fragrance retention, and can be blended with another fragrance to emphasize the top note and to enhance the feeling of cleanliness and refreshingness. It also is intended to provide 13-Methyl-9-cyclopentadecen-15-olide and a fragrance composition containing 13-methyl-9-cyclopentadecen-15-olide.

13-methyl-9-cyclopentadecen-15-olide

It is intended to provide a compound and a fragrance composition containing the compound, wherein the compound is useful as a fragrance, has floral and green odors in addition to a strong muguet odor, is stable in an aqueous vehicle, and can be blended with another fragrance to have enhanced freshness and diffusibility. It also is intended to provide 4,8-dimethyl-4,9-decadienenitrile and a fragrance composition containing 4,8-dimethyl-4,9-decadienenitrile.

4,8-dimethyl-4,9-decadienenitrile

A compound and a fragrance composition containing the same are provided, wherein the compound has a citrus odor in addition to a muguet odor, which is useful as a fragrance, is stable in an aqueous vehicle, and can provide a bright muguet odor with good fragrance retention by being blended with another fragrance. Particularly, they are 4(3)-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbonitrile and a fragrance composition containing 4(3)-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbonitrile.

4(3)-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbonitrile

The present invention relates to a process for producing (&#xb1;)-3a,6,6,9a-tetramethyl dodecahydronaphtho[2,1-b]furans from crude (&#xb1;)-3a,6,6,9a-tetramethyl dodecahydronaphtho[2,1-b]furans obtained by subjecting (&#xb1;)-3a,6,6,9a-tetramethyl dodecahydronaphtho[2,1-b]furan-2(1H)-ones which are produced by cyclizing a homofarnesylic acid amide or a monocyclohomofarnesylic acid amide in the presence of an acid agent and then hydrolyzing the cyclized product, to reduction reaction and then to cyclization reaction, said process including (i) an alkali treatment step in which the crude (&#xb1;)-3a,6,6,9a-tetramethyl dodecahydronaphtho[2,1-b]furans are heated in the presence of an alcohol and a metal hydroxide; and (ii) a washing treatment step in which the crude (&#xb1;)-3a,6,6,9a-tetramethyl dodecahydronaphtho[2,1-b]furans are washed with an aqueous acid solution. The thus obtained (&#xb1;)-3a,6,6,9a-tetramethyl dodecahydronaphtho[2,1-b]furans have a less off-odor and hardly suffer from deterioration of their smell during storage.

Process for producing (&#xb1;)-3a,6,6,9a-tetramethyldodecahydronaphtho [2,1-b]furans

The present invention relates to industrially useful production processes in which (&#xb1;)-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-ones and further (&#xb1;)-3a,6,6,9a-tetramethyldo decahydronaphtho[2,1-b]furans are produced from raw materials which are readily available at low costs, through short steps and in a simple manner. The process for producing (&#xb1;)-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-ones represented by the general formula (III): which includes the steps of cyclizing a homofarnesylic acid amide represented by the general formula (I): wherein Rand Rare each independently an alkyl group having 1 to 4 carbon atoms; and wavy lines each represents a carbon-to-carbon single bond having a cis or trans structure,and/or a monocyclohomofarnesylic acid amide represented by the general formula (II): wherein Rand Rand wavy lines are the same as defined above; and dotted lines represent that a carbon-to-carbon double bond is present at any of positions represented by the dotted lines,in the presence of an acid agent; and subjecting the cyclized product to hydrolysis.

Process for production of (&#xb1;)-3a,6,6,9a-Tetramethyldecahydronaphtho[2,1-b]Furan-2(1H)-one

Method for producing macrocyclic lactone

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.

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Wakayama, Japan

Takashi Aoki