2,5-Dimethyl-4-benzoquinone → 6-Hydroxy-4,4,5,8-tetramethylchroman-2-one

Participants

Reaction Steps

2,5-Dimethylbenzoquinone (10 g, 73.5 mmol) was dissolved in 300 mL of ether, which was mixed with an aqueous solution of sodium hydrosulfite (178 g in 150 mL of water, 85% pure, 870 mmol). The mixture was shaken until the ether layer became nearly colorless. The ether layer was separated, and the aqueous layer was extracted with ethyl ether (3×200 mL). The combined ether layers were washed with brine (2×150 mL) and dried over MgSO4. Filtration and solvent evaporation gave 10.03 g (72.6 mmol) of the hydroquinone as a white solid.

Provenance & Evidence