Homogentisic Acid → 2',5'-Dimethoxyacetophenone

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Reaction Steps

The best method known for preparing homogentisic acid appears to be that described in J. Biol. Chem. 179, 365 (1949), in which 1,4-dimethoxybenzene is reacted with acetyl chloride in the presence of aluminum chloride to give 2,5-dimethoxyacetophenone, the latter is reacted with sulphur in morpholine to give 2,5-dimethoxyphenylacetic acid, which on demethylation with hydrobromic acid gives homogentisic lactone, ring-opening of which gives the desired acid.

Provenance & Evidence