Acetic Acid → 4,4'-Dihydroxybenzil

Participants

Reaction Steps

Anisil (6.5 g), made by the oxidation of anisoin with copper sulphate in pyridine, was added to acetic acid (50 g) and heated to reflux to form a solution. Hydrobromic acid (s.g. 1.48) was added at reflux until anisil just started to precipitate (about 30 ml HBr being needed). After 2 hours' reflux, more hydrobromic acid (50 ml) was added, and the solution was refluxed for a further 2 hours. After this time, thin layer chromatography showed complete conversion into a single product. The solution was poured into cold water (600 ml) to precipitate a white solid. This was filtered off, washed with water and dried to give 5.5 g of 4,4'-dihydroxybenzil. This was used without further purification.

Provenance & Evidence