Process for preparing p-benzoquinone diketals

Details Process for preparing p-benzoquinone diketals Process for preparing p-benzoquinone diketals

C - Chemistry, Metallurgy

07

C

260/646.1, 204/4

C07C 43/18 (2006.01) C25B 3/02 (2006.01)

Patent

CA 1053707

Abstract of the Disclosure: p-Benzoquinone diketals of the formula Image wherein R is H, an alkyl group having from 1 to 4 carbon atoms or a halogen atom, preferably H, CH3, Cl of F, are prepared by anodic oxidation of benzene or alkoxybenzenes of the formula Image or Image wherein R has the aforesaid meaning and R1 is an alkyl radical having of from 1 to 4 carbon atoms in CH3OH containing a) less than about 5 % by weight of H2O as well as b) about 0.2 to 15 % by weight, calculated on the electrolyte, of at least a conducting salt selected from the group of ammonium and alkali flourides, perchlorates, nitrates, tetrafluoroborates, hexafluorosilicates, hexafluorophos- phates, benzene sulfonates, p-toluene sulfonates, quarte- nary ammonium and phosphonium fluorides as well as methyl- sulfates and additionally c) optionally about 0.5 to 10 % by weight, calculated on the electrolyte, of a base to be oxidized with difficulty, preferably 2,6-lutidine, at a known anode made of a conventional material, at a tempe- rature of from about -20 to +60°C. When using as starting ma- terial an alkoxybenzene wherein the group OR1 contains an al- kyl radical having of from 2 to 4 carbon atoms, the resultant p-benzoquinone tetramethyl diketal contains a small quantity of the corresponding trimethyl alkyl diketal having an alkyl group of from 2 to 4 carbon atoms in the alkoxy group. The diketals obtained may be converted into the corresponding p- quinones by acidic hydrolysis and are, consequently valuable intermediates for the preparation of the latters as well as for the transformation into the corresponding hydroquinones, which in their turn may be used in known manner in photgra- phic, as stabilizers for monomers, as starting material for the dyestuff preparation etc.

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