Sumitomo Chemical Company, Limited

Yamanouchi Pharmaceutical Company Ltd.

Makoto Nakamura

Shinichi Hasegawa

Tsutomu Chiyoda

Fujio Masuko

Gohfu Suzukamo

Yuzo Maegawa

Kazuhiko Hamada

Seiichi Kai

Nobuharu Kono

Kouichi Watanabe

Crystal form of benzodiazepine derivatives

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 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

A process for producing phloroglucin important as an intermediate compound of medicine, sensitizer and the like which comprises reacting an oxidation product containing at least one carbinol compound of carbinol dihydroperoxide, dicarbinol hydroperoxide and tricarbinol obtained by oxidation of 1,3,5-triisopropylbenzene, with hydrogen peroxide in a heterogeneous system in the presence of an acid catalyst and an organic solvent inert to the hydrogen peroxide and capable of dissolving the oxidation product, and decomposing the reaction product with an acid.

Process for producing phloroglucin

In a method for producing phloroglucin by a decomposition of 1,3,5-triisopropylbenzene trihydroperoxide (hereinafter referred to as THPO), a method for producing phloroglucin wherein an acid catalytic decomposition is carried out under the condition that:

Method for producing phloroglucin

A method for purifying phloroglucin wherein crude phloroglucin obtained by an acid-decomposition of 1,3,5-triisopropylbenzene trihydroperoxide in the presence of a solvent and removal of the formed acetone and the solvent by evaporation, is extraction-treated within a pH range of 7.5 to 12 in the coexistence of an aqueous alkali liquor of 4 to 25 times by weight based on the crude phloroglucin and an organic solvent of 0.05 to 6 times by weight based on said aqueous alkali liquor selected from ketones and esters which are separable from the aqueous alkali liquor, and after acidifying the separated aqueous alkali extract, the deposited crystal is recrystalized. The phloroglucin is useful as a starting material of medicines and photosensitizers.

Method for purifying phloroglucin

In a method for producing 1,3,5-triisopropylbenzene trihydroperoxides by bringing 1,3,5-triisopropylbenzene or its homologs into contact reaction with oxygen or an oxygen-containing gas in the co-existence of an aqueous alkali solution, a method for producing 1,3,5-triisopropylbenzene trihydroperoxides wherein said contact reaction is carried out under a condition that the reaction temperature be 60.degree. to 120.degree. C., the pH of the reaction solution phase be 8 to 11 and the amount of said aqueous alkali solution be 0.1 to 3 times by weight based on the organic layer as raw material, the reaction is finished at a point when the yield of 1,3,5-triisopropylbenzene trihydroperoxide (hereinafter referred to as THPO) is not less than 20% and besides, the total of the yield of carbinols (hereinafter referred to as THPO carbinols) having a structure in which part or all of the three hydroperoxy groups of THPO have been replaced by hydroxy groups and that of THPO above is not less than 60%, and if necessary, after separation-removing the aqueous layer from the resulting oxidation solution, the organic layer is, as such or as an organic layer containing THPO and THPO carbinols after removing reaction intermediates from it, brought into contact with hydrogen peroxide. The 1,3,5-triisopropylbenzene trihydroperoxide are useful as a starting material of phloroglucin.

Method for producing 1,3,5-triisopropylbenzene trihydroperoxides

A process for producing 2-hydroxynaphthalene-3-carboxylic acid comprising reacting carbon dioxide with a homogeneous liquid mixture comprising an alkali metal salt of .beta.-naphthol, .beta.-naphthol and a specific alkylbenzene is disclosed.

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Ibaraki, Japan

Makoto Nakamura