m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

Participants

Reaction Conditions

Reaction Steps

106.5 g of m-Chloroperbenzoic acid (70%) was charged portionwise to the vessel containing the cooled (10-15° C.) solution of 69.5 g of the N-(cyclohex-3-en-1(R)-yl)-2,2,2-trifluoro-acetamide of step A maintaining temperature <30° C., and rinsed through with 69.5 ml of chlorobenzene. The mixture obtained was stirred at 20 to 25° C. for 1 h and the reaction was followed by TLC until completion. Upon completion of the reaction, the mixture obtained was cooled to 0 to −5° C., stirred for 30 min and the solid precipitate (mCBA) obtained was filtered off and washed with 2×34.8 ml of chlorobenzene. The resultant filtrate was washed with 347.6 ml of 10% sodium thiosulfate solution to remove peroxides, and the resultant aqueous layer was back extracted with 208.6 ml of chlorobenzene. The combined organic layers obtained were washed with 347.6 ml of 5% sodium bicarbonate solution to ensure a pH>7 of the aqueous phase and the resultant aqueous layer was back extracted with 208.6 ml of chlorobenzene. The combined organic layers were washed with 347.6 ml of water.

Provenance & Evidence