Sumitomo Chemical Company, Limited

Seiichi Kai

Masayoshi Minai

Yuji Ueda

Takayuki Higashii

Takaharu Ikeda

Michitada Kondo

Kunihiko Tanaka

Hirokazu Hosaka

Kenji Tanimoto

Hideyuki Ikehira

Makoto Nakamura

Katsuyuki Shiota

Nobuharu Kono

Toshiharu Morita

Sachiko Imazu

Process for preparing haloketo acid derivatives [I]: ##STR1## wherein R is H or C.sub.1-6 alkyl, and X is chlorine or bromine, which comprises reacting .beta.-oxo-acid ester [II]: ##STR2## wherein R.sup.1 is H or C.sub.1-6 alkyl, R.sup.2 is C.sub.1-5 alkyl or OR.sup.3 (R.sup.3 is C.sub.1-6 alkyl), and X is the same as above, with nitrosating agent [IV]:

Process for preparing haloketo acid derivatives

Acylaromatic compounds ##STR1## (Q: aromatic compound residue; R: straight, branched or cyclic aliphatic group, aromatic group or araliphatic group) are prepared in high yield by a reaction, in the presence of a boron trifluoride complex catalyst, of an aromatic compound with ##STR2## (X: H, Cl, Br; Y: Cl, Br) or with RCOOH in the presence of (XYCHCO).sub.2 O.

Process for producing acylaromatic compounds

Process for preparing haloketo acid derivatives [I]: ##STR1## wherein R is H or C.sub.1-6 alkyl, and X is chlorine or bromine, which comprises reacting .beta.-oxo-acid ester [II]: ##STR2## wherein R.sup.1 is C.sub.1-6 alkyl, R.sup.2 is C.sub.1-5 alkyl or OR.sup.3 (R.sup.3 is C.sub.1-6 alkyl), and X is the same as above, with nitrosating agent [IV]:

An improved process for preparing an optically active 4-hydroxycyclopentenone of the formula: ##STR1## wherein R is a lower alkyl, the symbol  means double bond or triple bond, and the * marked carbon is an asymmetric carbon, and the corresponding racemic 4-hydroxycyclopentenone, which are useful as an intermediate for preparing medicinal or agricultural products, particularly pharmaceutically active prostaglandins, and intermediates for preparing the optically active and/or racemic 4-hydroxycyclopentenone.

Process for preparing optically active cyclopentenones

A process for preparing an optically active cyclopentenone of the formula: ##STR1## wherein R is a hydrogen atom or a lower alkyl group and n is an integer of 4 to 8, which comprises contacting a dl-cyclopentenone ester of the formula: ##STR2## wherein R and n are each as defined above and R' is a lower alkyl group optionally substituted with halogen on an enzyme having a capability of hydrolyzing selectively either one of the d- or l-form isomer in the dl-cyclopentenone ester (II) in an aqueous medium for asymmetric hydrolysis.

Production of cyclopentenones by enzyme resolution

2-Acylfuran derivatives ##STR1## (R: alkyl, phenyl, etc.; R.sub.1 : H, alkyl) are prepared in high yield by reaction, in the presence of a boron trifluoride complex catalyst, of a furan compound ##STR2## (X: H, Cl, Br; Y: Cl, Br) or with RCOOH in the presence of (XYCHCO).sub.2 O.

Process for producing 2-aceylfuran derivatives

A method for producing m-hydroxy-acetophenone which comprises allowing m-(2-hydroxy-2-propyl)cumene hydroperoxide to react at 30.degree. to 100.degree. C. in the presence of an aqueous solution containing 0.001 to 1 mole of iron salt per mole of said compound, 0.01 to 4 moles of copper salt per mole of said iron salt, and mineral acid to give m-(2-hydroxy-2-propyl)acetophenone, then allowing the resulting compound to react at 30.degree. to 95.degree. C. in the presence of 1 to 20 moles of 5 to 90% by weight aqueous hydrogen peroxide solution per mole of said compound and acid catalyst to form m-(2-hydroperoxy-2-propyl)acetophenone, and further subjecting the product formed to acid decomposition. m-Hydroxyacetophenone is an important intermediate in the fields of pharmaceuticals, agricultural chemicals, dyestuffs and the like.

Process for producing m-hydroxyacetophenone

Acetone having a markedly low content of aldehydes is recovered from an aqueous rectification residue brought about by rectification of crude acetone carried out after one crude acetone having been alkali-treated or while an alkali or an aqueous solution thereof being added to the crude acetone, by mixing the aqueous rectification residue with an alkali, neutralizing the mixture to a pH of 4 to 9, and then subjecting the resulting mixture to distillation to obtain acetone as a distillate.

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Nara, Japan

Seiichi Kai