Acetoacetic Acid → Hydroquinone mono-acetate

Participants

Reaction Steps

The preparation of monoacetates of hydroquinone and catechol has been investigated, according to early publications, with varying results. Oltcott (J. Am. Chem. Soc. 59, 1937, 392-393) has found, that the monacetylation of these two dihydroxybenzenes can be performed by careful reaction with an acetylating agent, e.g. acetic anhydride, in aqueous alkaline solution. The desired mono-acetate was obtained in a yield of only 20-30%, whereas the major product obtained was the diacetate. Johnston (Chem. Ind. 1982, 1000) has succeeded in improving the formation of the mono-acetate of hydroquinone from hydroquinone and acetic anhydride by using triethyl amine as a base and 4-dimethylaminopyridine (DMAP) as a catalyst, in a polar organic solvent, viz. in ethyl acetate solution. Under such reaction conditions, Johnston has succeeded in obtaining hydroquinone mono-acetate in yields of 58-65%.

Provenance & Evidence