Sumitomo Chemical Company, Limited

Kazuhiko Hamada

Gohfu Suzukamo

Yukio Yoneyoshi

Toshio Nishioka

Masayoshi Minai

Koichi Fujisawa

Tsuneyuki Nagase

Tadashi Katsura

Gohu Suzukamo

Fujio Masuko

Makoto Nakamura

Tadatoshi Aratani

Hiroshi Yoshihara

Kanji Nishizawa

Goufu Suzukamo

The present invention relates to an asymmetrically modified borohydride type compound obtained by reacting an optically active amino alcohol represented by the formula, ##STR1## or its salt with an acid with a borohydride compound; its production method; and a method for producing an optically active alcohol derivative useful as fungicides, herbicides or plant growth regulators and represented by the formula, ##STR2## which comprises asymmetrically reducing a ketone compound represented by the formula, ##STR3## with the asymmetrically modified borohydride type compound.

Asymmetrically modified boron hydride type compound and a method for

The present invention relates to an optically active borane complex represented by the general formula, ##STR1## wherein R.sup.1 represents an aryl group, R.sup.2 represents an alkyl group and a mark * means an asymmetric carbon, and a method for producing optically active alcohol derivatives by the reduction of prochiral ketones with said borane complex. The optically active alcohol derivative is useful for fungicides, herbicides or plant growth regulators.

Optically active borane complex and a method for producing an optically

Asymmetrically modified boron hydride type compound, a production method

In a Reimer-Tiemann reaction for the preparation of a mixture of two hydroxybenzaldehydes (i.e., salicylaldehyde and p-hydroxybenzaldehyde) by reacting phenol with chloroform and an aqueous alkali solution in a heterogeneous system, the two hydroxybenzaldehydes can be prepared in a controlled formation ratio, yield and reaction rate depending upon the conditions used when the reaction is carried out in the presence of a phase transfer catalyst selected from the group consisting of a cationic type phase transfer catalyst, an amphoteric type phase transfer catalyst and an anionic type phase transfer catalyst.

Process for the preparation of hydroxybenzaldehydes

A method for producing an optically active 2,2-dimethylcyclopropanecarboxylic acid useful as an intermediate for dehydropeptidase I inhibitors, medicines and agricultural chemicals, which comprises reacting an optically active diphenylethylamine represented by the formula, ##STR1## wherein R.sub.1 and R.sub.2 are each a hydrogen atom or a lower alkyl group, with 2,2-dimethylcyclopropanecarboxylic acid in a solvent to achieve the optical purification of said acid.

Method for producing an optically active

In a Reimer-Tiemann reaction for the preparation of a mixture of salicylaldehyde and p-hydroxybenzaldehyde, improved yield of the product and high selectivity of salicylaldehyde can be obtained when an alkali metal salt of a phenol is reacted with a reaction mixture comprised of chloroform and a slurry of an alkali metal hydroxide (preferably, in a fine powder state thereof) and an inert organic solvent and optionally, a catalytic amount of a surfactant.

Process for preparation of hydroxybenzaldehydes

A 4-hydroxybenzaldehyde derivative of the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is selected from the group consisting of hydrogen atom, halogen atoms, lower alkyl groups or lower alkoxy groups, which is useful as intermediate for the production of medicines or agricultural chemicals, or as flavor, is produced by the reaction of a p-cresol derivative of the formula: ##STR2## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is as defined above, with oxygen or oxygen-containing gas in the presence of a base and a catalytic amount of cobalt compound or metallic cobalt.

Preparation of p-hydroxybenzaldehyde derivatives

A process for producing 5-halomethylfurfural represented by the formula, ##STR1## wherein X is Cl or Br, which comprises carrying out a acid-decomposition of saccharide in a water/organic solvent/magnesium halide system with hydrochloric acid, sulfuric acid, hydrogen chloride or other mineral acid in the presence or absence of surface active agent as a catalyst. The 5-halomethylfurfural is useful as an intermediate of medicines, agricultural chemicals, perfumes and the like.

Process for producing 5-halomethylfurfural

A process for producing 5-methylfurfural by reducing 5-chloromethylfurfural which is used as a starting material or to be obtained by decomposing glucides commercially available more cheaply with hydrochloric acid, with hydrogen in an organic solvent in the presence of a palladium catalyst.

Process for producing 5-methylfurfural

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.

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Ibaraki, Japan

Kazuhiko Hamada