Benzyl Chloride → 2,2-Dimethylpropanoic acid, 2,3,5-trimethyl-4-(phenylmethoxy)phenyl ester

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Reaction Steps

A mixture of 43.5 g (184 mmol) of 2,2-dimethylpropanoic acid, 4-hydroxy-2,3,6-trimethylphenyl ester (Example A), 23.4 g (184 mmol) of benzyl chloride and 30.5 g (1.2×184 mmol) of anhydrous potassium carbonate in 500 mL of acetonitrile is stirred at reflux for 70 hours. The solid is removed and the reaction flask and solid are washed with fresh acetonitrile and the solvent removed on a rotary evaporator. The crude product amounts to 60.5 g which crystallizes on standing, mp 50°-53° C. Recrystallization from methanol in the presence of charcoal affords the title compound; mp 58°-59° C.

Provenance & Evidence