m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

Temperature

22.5 °C

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.

1. additioncontaining the
2. washrinsed through with 69.5 ml of chlorobenzene
3. customThe mixture obtained
4. customUpon completion of the reaction
5. customthe mixture obtained
6. temperaturewas cooled to 0 to −5° C.
7. stirringstirred for 30 min

ORD record

ord-f55a149c586248b2876e29334012cb84

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09120727B2