Ethyl Acetate → 1-(2-Hydroxyphenyl)-2-methyl-1-propanone

Participants

Reaction Conditions

Reaction Steps

100 ml of sec-butyllithium at 1.4 M in cyclohexane were added dropwise to a solution of 31.59 g (130 mmol) of 2-bromophenyl isobutyrate in 300 ml of tetrahydrofuran at −85° C. under nitrogen. The reaction medium was maintained for 30 minutes at approximately −75° C. and was then left to gently return to ambient temperature. After 2 hours, a little ethyl acetate was added, followed by approximately 400 ml of a 1 M aqueous sodium dihydrogen carbonate solution. The organic phase was recovered, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated. 23.97 g of an orange oil were obtained and purified on silica cake. The residue obtained was chromatographed on a prepacked silica column (eluent heptane/ethyl acetate). 4.3 g of product were obtained in the form of a yellow oil. Yield=20%.

Provenance & Evidence