Acetone → 2-Acetoxyphenoxyethyl Alcohol

Participants

Reaction Steps

2-(2-Hydroxyethoxy)phenol (308 g; 2 mol) was taken up in a 5L Erlnmeyer flask fitted with mechanical stirrer. Anhydrous acetone (4L, dried over K2CO3), and potassium carbonate powder (290 g; 2.1 mol) were added, and the mixture was stirred vigourously. Acetic anhydride (207 mL; 2.2 mol) was added from an additional funnel slowly over a period of 1 hour. Stirring was continued for 3 hors. TLC (CH2Cl2/MeOH: 9:1, v/v) showed disappearance of starting material. The reaction mixture was filtered, solid washed thoroughly with acetone (1L). The combined fractions was concentrated and purified by chromatography eluting with hexane and ethyl acetate (0% to 35% EtOAc; v/v). The product was obtained as a colorless viscous oil. Yield 258-264 gms (70-72%).

Provenance & Evidence