Sumitomo Chemical Company, Limited

Sumika Fine Chemicals, Co.,ltd.

Daili Chemical Company, Limited

Norio Kometani

Toshio Nakamatsu

Gohfu Suzukamo

Kenji Saito

Yukio Yoneyoshi

Yasuhiro Nishida

Azusa Fujiwara

Yoshiaki Hayashi

Masanobu Terao

Shinichi Watanabe

Shigetoshi Muneishi

The present invention relates to a process for producing optically active halomethyl phenyl carbinols of the formula (1), comprising reducing halomethyl phenyl ketones of the formula (2) using an asymmetric reducing agent obtained from boranes and optically active .alpha.-phenyl-substituted-.beta.-amino alcohols of the formula (3) or optically active .alpha.-non-substituted-.beta.-amino alcohols of the formula (4). The present invention further relates to a process for producing optically active carbinols, comprising reacting a prochiral ketone with, an asymmetric reducing agent obtained from optically active .beta.-amino alcohols of the formula (5), a metal boron hydride and Lewis acid or lower dialkyl sulfuric acid. All of the formulas (1) to (5) are the same as shown in the specification.

Process for producing optically active carbinols

The present invention relates to a process for producing optically active halomethyl phenyl carbinols of the formula (1), comprising reducing halomethyl phenyl ketones of the formula (2) using an asymmetric reducing agent obtained from boranes and optically active .alpha.-phenyl-substituted-.beta.-amino alcohols of the formula (3) or optically active .alpha.-non-substituted-.beta.-amino alcohols of the formula (4). The present invention further relates to a process for producing optically active carbinols, comprising reacting a prochiral keytone with an asymmetric reducing agent obtained from optically active .beta.-amino alcohols of the formula (5), a metal boron hydride and Lewis acid or lower dialkyl sulfuric acid. All of the formulas (1) to (5) are the same as shown in the specification.

The present invention provides a process for producing (R)-styrene oxides represented by the formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and X are as defined in the specification, which comprises treating a mixture of (R)- and (S)-phenylhalogenomethylcarbinols with a lipase in the presence of a carboxylate to preferentially convert the (S)-phenylhalogenomethylcarbinols, and treating a mixture of the formed carbinol alkylates (3) and (R)-phenylhalogenomethylcarbinols with a base to cyclize the (R)-phenylhalogenomethylcarbinols, and also provides an industrially excellent process for producing (R)-styrene oxides (1) which comprises using a mixture enriched with (R)-phenylhalogenomethylcarbinols as the mixture of (R)- and (S)-phenylhalogenomethylcarbinols (2).

Process for producing (R)-styrene oxides

A method for producing 1,4-dihydroxy-2-naphthoic acid which comprises the steps of: subjecting 1,4-dihydroxynaphthalene into an alkali metal salt formation reaction in an organic medium capable of dissolving 1,4-dihydroxynaphthalene using an alkali metal alcoholate; and subjecting the salt formation reaction mixture to carboxylation using carbon dioxide gas.

Method for producing 1,4-dihydroxy-2-naphthoic acid

A method for producing 2,6-dihydroxybenzoic acid, which comprises heating an aqueous solution which contains a mixture of 2,6-dihydroxybenzoic acid and 2,4-dihydroxybenzoic acid and has a pH value of 4 or more, to selectively decompose 2,4-dihydroxybenzoic acid, and separating 2,6-dihydroxybenzoic acid from the decomposition reaction mixture.

Method for producing 2,6-dihydroxybenzoic acid

A process for producing 2-methyl-1,3-cyclohexanedione which comprises subjecting 1,3-cyclohexanedione, formaldehyde and a dialkylamine to Mannich reaction to obtain a 2-dialkylaminomethyl-1,3-cyclohexanedione, and subjecting the 2-dialkylaminomethyl to hydrogenolysis, and a process for producing 2-methylresorcinol which comprises aromatizing 2-methyl-1,3-cyclohexanedione obtained. According to these processes, it is possible to produce high-purity 2-methylresorcinol and 2-methyl-1,3-cyclohexanedione commercially easily and advantageously.

Process for producing 2-methyl-1,3-cyclohexanedione and

An anthrapyridone compound of the following formula (I), which is useful for coloring synthetic resins: ##STR1## wherein Q is --NH.sub.2, --NHCH.sub.3 or --NHCOZ where Z is phenyl or alkyl which may be substituted; X.sub.1, X.sub.2 and X.sub.3 are each hydrogen, halogen, alkyl, alkoxy, hydroxy, --NHCOR.sup.1, --CONR.sup.2 R.sup.3 m --COR.sup.4, --COOR.sup.5, --SO.sub.2 R.sup.6 or --SO.sub.2 NR.sup.7 R.sup.8 where R.sup.1 and R.sup.4 are each C.sub.1-4 alkyl, R.sup.2 and R.sup.3 are each hydrogen or C.sub.1-4 alkyl, R.sup.5 and R.sup.6 are each alkyl or hydroxyalkyl and R.sup.7 and R.sup.8 are each hydrogen or C.sub.1-4 alkyl, with proviso that when Q is --NHCH.sub.3, X.sub.1, X.sub.2 and X.sub.3 are each hydrogen, halogen, alkoxy, hydroxy, --NHCOR.sup.1, --CONR.sup.2 R.sup.3, --COR.sup.4, --COOR.sup.5, --SO.sub.2 R.sup.6 or --SO.sub.2 NR.sup.7 R.sup.8. Process for producing the anthrapyridone compound is also provided.

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Kishiwada, Japan

Norio Kometani