Benzyl Alcohol → 3-(Benzyloxy)-3-oxopropanoic acid

Participants

Reaction Steps

A solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (25 g, 174 mmol) and benzyl alcohol (36 mL, 347 mmol) in toluene (100 mL) was heated at 106° C. for 24 h. The solution was poured into 5% Na2CO3 (aqueous), the organic layer was separated, and the aqueous layer was washed with ether (3×). The aqueous layer was then acidified with 1N HCl and extracted with ethyl acetate (2×). The combined ethyl acetate extracts were dried over anhydrous MgSO4, filtered and evaporated at reduced pressure to give malonic acid monobenzyl ester (11.42 g, 34%).

Provenance & Evidence