Sumitomo Chemical Company, Limited

Gohu Suzukamo

Tsuneyuki Nagase

Kiyoshi Ikimi

Tetsuo Takano

Mitsuhisa Tamura

Yoshio Suzuki

Masami Fukao

Masaru Ishino

Motoo Hazama

Kazuhiko Hamada

Tadatoshi Aratani

Ken-ichi Hirose

Takeo Takahashi

Horosuke Toshioka

Hirosuke Yoshioka

Process for preparing predominantly Z-substituted allylic alcohols of the formula: ##STR1## wherein R.sup.1 is a straight or branched C.sub.1 -C.sub.25 alkyl group optionally bearing at least one substituent and/or at least one unsaturated linkage and R.sup.2 is a hydrogen atom or a methyl group, which comprises reacting a vinyl epoxide of the formula: ##STR2## wherein R.sup.2 is as defined above with an organolithium compound of the formula above. More particularly, there is disclosed a process for R.sup.1 --Li wherein R.sup.1 is as defined above; particularly, process for preparing .alpha.-santalol of the formula: ##STR3## which comprises reacting 3-methyl-3,4-epoxybutene-1 with lithiomethyl-2,3-dimethyltricyclo[2.2.1.0.sup.2,6 ]heptane.

Process for producing allylic alcohols

A novel optically active cis-4,5-disubstituted imidazolidin-2-one derivative of the formula: ##STR1## wherein R.sup.1 is a C.sub.1 -C.sub.4 alkyl group or benzyl and R.sup.2 is a chiral aralkyl group optionally having at least one of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and hydroxyl groups is produced asymmetrically by the reaction of 1,3-dibenzyl-cis-4,5-dicarboxy-imidazolidin-2-one or its anhydride with an optically active secondary amine of the formula: ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above and is transformed into the lactone of 1,3-dibenzyl-cis-4-carboxy-5-hydroxymethyl-imidazolidin-2-one, which is a key intermediate in the synthesis of d-biotin.

Optically active imidazolidin-2-one derivatives

Rose oxide, which is an important olfactive compound valuable in the art of perfumery, is advantageously produced from citronellol through a novel synthetic route comprising

Process for producing 2-(2'-methyl-1'-propenyl)-4-methyltetrahydropyran

A process for preparing an arylacetaldehyde by reacting the corresponding arylmethyl halide with carbon monoxide and hydrogen in the presence of a cobalt compound and a basic reagent in a liquid medium, characterized in that the basic reagent is an alkali metal compound and the liquid medium is a solvent system chosen from nitriles and their mixtures with hydrocarbons, whereby the arylacetaldehyde can be produced in a good yield by the use of a small amount of the cobalt compound as the catalyst.

Process for preparing arylacetaldehydes

An alcohol is produced in a high selectivity with a good yield from the corresponding carboxylic acid by reducing the latter with hydrogen in the presence of a rhenium catalyst in the coexistence of an organic base. An arylacetic acid, which is included in the starting carboxylic acid, can be produced in an excellent yield from the corresponding aryl aldehyde by reacting the latter with carbon monoxide and water in the presence of rhodium or its compound and hydrogen iodide.

Process for preparing alcohols

A method for racemization of optically active amines which comprises contacting an optically active amine of the formula: ##STR1## wherein C* is an asymmetric carbon atom, R.sub.1 is alkyl, aralkyl or aryl and R.sub.2 is aryl or alkoxycarbonyl, the aryl or aralkyl moiety bearing optionally one or more alkyl or alkoxy groups on the aromatic ring, provided that R.sub.1 and R.sub.2 are always different from each other, with a catalyst comprising an alkali metal and a polycyclic aromatic hydrocarbon until a sufficient amount of the optically active amine is racemized.

Method for racemization of optically active amines

A method for racemization of optically active 2,2-dimethyl-3-(1'-alkenyl)-cyclopropane-1-carboxylic acids of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each a hydrogen atom or an alkyl group having 1 to 4 carbon atoms or, when taken together with the carbon atom to which they are attached, represent a cycloalkylidene group having 4 to 6 carbon atoms, which comprises the step of contacting the corresponding acid halide with boron halide at a temperature of not more than 20.degree. C.

Racemization of optically active

An optically active lysine alkyl ester.dihydrochloride is racemized by heating at 100.degree. C. to 250.degree. C. under an atmosphere of hydrogen. By combining this process with asymmetric hydrolysis of racemic lysine alkyl ester with enzymes, racemic lysine alkyl ester can be converted all to L-lysine.

Racemization of an optically active lysine alkyl ester

A process for producing furan derivatives of the formula, ##STR1## wherein R is hydrogen, methyl or chloromethyl, which comprises reacting a mono- or a disaccharide with hydrochloric acid in a mixture containing water, an organic solvent and a catalytic amount of a surface active agent.

Process for producing a furan derivative

A method for racemization of optically active 2,2-dimethyl-3-(1'-alkenyl)-cyclopropane-1-carboxylic acids of the formula: ##EQU1## wherein R.sub.1 and R.sub.2 are each a hydrogen atom or an alkyl group having 1 to 4 carbon atoms or, when taken together with the carbon atom to which they are attached, represent a cycloalkylidene group having 4 to 6 carbon atoms, which comprises the step of contacting the corresponding acid halide with a Lewis acid.

A method for racemization of optically active amines which comprises contacting an optically active amine of the formula: ##EQU1## wherein C* is an asymmetric carbon atom, R.sub.1 is alkyl, aralkyl or aryl and R.sub.2 is aryl or alkoxycarbonyl, the aryl or aralkyl moiety bearing optionally one or more alkyl or alkoxy groups on the aromatic ring, provided that R.sub.1 and R.sub.2 are always different from each other, with an alkali metal catalyst selected from the group consisting of (1) an alkali metal deposited on a solid carrier, (2) an alkali metal dispersed in a liquid medium and (3) an alkali metal alloy at a temperature of from -10.degree. to 50.degree.C until a sufficient amount of the optically active amine is recemized.

Racemization of optically active amines

A process for preparing trans-chrysanthemic acid which comprises reacting a mixture of alkyl trans-chrysanthemate and alkyl cis-chrysanthemate with an equimolar amount or less of an alkali with respect to the trans-isomer in the presence of water or an alcohol to hydrolyze the trans-isomer predominantly and separating the hydrolyzed trans-isomer from the unreacted cis-isomer.

Process for preparing trans-chrysanthemic acid

Alkyl cis-chrysanthemate is treated with a catalytic amount of alkali metal alkoxide at a temperature of about 50.degree. to 200.degree.C in the absence or presence of an aprotic solvent to give alkyl trans-chrysanthemate in a high purity and an excellent yield.

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Ibaraki, Japan

Gohu Suzukamo