Preparation of 2,3,5-trimethyl-p-benzoquinone

Details Preparation of 2,3,5-trimethyl-p-benzoquinone Preparation of 2,3,5-trimethyl-p-benzoquinone

C - Chemistry, Metallurgy

07

C

260/396

C07C 50/04 (2006.01) C07C 46/06 (2006.01) C07C 46/08 (2006.01) C07C 46/10 (2006.01)

Patent

CA 1234132

Abstract of the Disclosure: Trimethyl-p-benzoquinone of the formula I Image (I) is prepared by a process wherein A. 2,5,6-trimethylcyclohex-2-en-1-one or 2,3,6-trimethyl- cyclohex-2-en-1-one is reacted with air or oxygen at from 0 to 150°C in a virtually anhydrous low molecular weight alkanol in the presence of a catalytic amount of copper (I) oxide or copper(II) oxide and in the presence of from 1 to 10 moles of a hydrogen halide gas per mole of tri- methylcyclohexenone, and thereafter B. the reaction mixture, which essentially contains 2,3,6-trimethylphenol and/or 4-halo-2,3,6-trimethylphenol, is mixed with an alkali metal alcoholate in an amount such that a sample, when moistened with water, has a pH of from 3 to 6, and is then reacted with air, pure oxygen or tert.-butyl hydroperoxide at from 0 to 150°C, or wherein from 1 to 10 mole equivalents of a hydrogen halide gas per mole of substrate to be reacted are passed into a mixture containing a virtually anhydrous low mole- cular weight alkanol and a catalytic amount of copper(I) oxide or copper(II) oxide at from 0 to 30°C, an alkali metal alcoholate is addled in an amount such that a sample, when moistened with water, has a pH of from 3 to 6, about one mole equivalent of 2,3,6-trimethylphenol is added and the mixture is then reacted with air, oxygen or tert.-butyl peroxide at from 0 to 150°. Trimethyl-p-benzoquinone is an important intermediate for the synthesis of vitamin E.

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