Acetic Acid → HCID 71548220, compound

Participants

Reaction Steps

To a stirred solution of ethoxy-alcohol 52 (30 g, 0.085 mol) in dichloromethane (300 ml) was added catalytic TEMPO (0.265 g, 0.0017 mol) and stirred for 10 minutes. To the above solution 100 ml aqueous solution containing mixture of sodium chlorite (23 g, 0.25 mol) and potassium bromide (5 g, 0.0425 mol) was added and stirred for 5 minutes. To this reaction mixture was added aq. acetic acid (5 ml, 20%) and stirring was continued for 12 hour at ambient temperature. The reaction mixture was filtered and the solid was washed with D.M. Water (500 ml) followed by washing with dichloromethane (200 ml). Toluene (400 ml) was added to the solid obtained and the resulting mixture was concentrated azeotropically till the volume of mixture remains to 150 ml and cooled in ice bath. The resulting suspension was filtered. The solid obtained was washed with hexane and dried in vacuum to yield ethoxy-acid 53 (25 g, 80.6%).

Provenance & Evidence