Hydrogen Bromide → 2,6-Di-tert-butylhydroquinone

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Reaction Steps

A solution of 2,6-di-tert.butyl-phenol (11 g, 53.3 mmol), hydrogen peroxide at 60% (8 ml) and hydrogen bromide (5 g, 61.7 mmol) in methanol (150 ml) is refluxed for 25 minutes. On concentrating the solution, 2,6-di-tert.butyl-1,4-benzoquinone (10.5 g, 89.4%) crystallizes. This product is hydrogenated, in methanol (110 ml), in autoclave, with Pd/C at 5% (0.12 g), under a hydrogen pressure of 10 kg/cm2, for 50 minutes, at 20° C. After the catalyst being filtered off, and solvent evaporation, 2,6-di-tert.butyl-hydroquinone is obtained with a yield of 97%.

Provenance & Evidence