Phenylacetone → Ethyl 3-hydroxy-3-methyl-4-phenylbutanoate

Participants

Reaction Steps

A mixture of benzyl methyl ketone (134 g, 1 mole) and ethyl bromoacetate (168 g, 1 mole) was added to a mixture of mossy zinc (100 g) in toluene (500 cm3) in a large flask. When the vigorous exothermic reaction had subsided, the mixture was boiled for 3 hours. The solution was cooled, and washed sequentially with dilute sulfuric acid, 10% aqueous sodium hydroxide and then with water. The organic layer was separated, dried and filtered. The toluene solvent was removed, leaving the hydroxy ester, ethyl 3-hydroxy-3-benzylbutanoate (152.8 g), as an orange oil. The ester's structure and purity were established by NMR spectroscopy.

Provenance & Evidence