Phenacyl bromide → alpha-Hydroxyacetophenone

Participants

Reaction Steps

85% Ethanolic solution (1200 mL) of 2-bromo-1-phenylethanone (99.52 g, 500 mmol) and sodium formate (215.0 g, 3160 mol) was heated to reflux for 5 hours. After the solvent was evaporated in vacuo, water (1000 mL) was added to the residue and extraction with ethyl acetate was conducted. The organic layers were combined and dried over anhydrous sodium sulfate and the solvent was evaporated therefrom in vacuo. Petroleum ether was added to the residual oily product to crystallize whereupon 2-hydroxy-1-phenylethanone (59.67 g, 88%) was produced. Mp. 86-89° C. 1H-NMR (DMSO-d6) δ: 4.81 (d, J=5.8 Hz, 2H), 5.07 (t, J=5.8 Hz, 1H), 7.50-7.55 (m, 2H), 7.63-7.67 (m, 1H), 7.92-7.95 (m, 2H)

Provenance & Evidence