4-Methylcatechol → 4-Methyl-5-phenylsulphonyl-1,2-benzenediol

Participants

Reaction Steps

A solution of 50 g (152 mmol) of potassium hexacyanoferrate (III) and 95 g of sodium acetate trihydrate in 200 ml of water is added dropwise in the course of 30 minutes, at room temperature under nitrogen, to a solution of 16.4 g (100 mmol) of the sodium salt of benzenesulphinic acid and 13.6 g (110 mmol) of 4-methyl-1,2-benzenediol in 150 ml of water. After stirring for 11/2 hours, the reaction mixture is acidified and repeatedly extracted with ethyl acetate. The combined organic phases are washed with water and saturated sodium chloride solution, dried over sodium sulphate and concentrated by evaporation. The residue is recrystallised from ether/hexane, yielding 4-methyl-5-phenylsulphonyl-1,2-benzenediol having a melting point of 145°-149°.

Provenance & Evidence