m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

Participants

Reaction Steps

is stirred with 0.84 g (4.15 mmol) of 85% strength m-chloroperbenzoic acid in 50 ml of methylene chloride at room temperature for 2 days. The precipitate is filtered off with suction, stirred with 50 ml of diethyl ether and filtered off with suction again. The solid residue is dissolved in 2N HCl and the acid aqueous solution is extracted several times by shaking with diethyl ether and finally concentrated completely. The residue is extracted with hot ethanol in several portions. The ethanol extracts are concentrated and the residue is dried. 0.44 g (45.5% of theory) of the m-chlorobenzoic acid salt of the N1 -oxide of 9-[(1RS,4SR)-4-hydroxy-cyclo-pent-2-en-1-yl]adenine of melting point 198°-200° C. is obtained. 1H NMR (270 MHz, d6 -DMSO), δ[ppm]: 8.66 (s, 1H), 8.27 (s, broad, 1H), 8.22 (s, 1H), 7.89 (m, 2H), 7.70 (m, 1H), 7.53 (m, 1H), 6.20 (m, 1H), 6.04 (m, 1H), 5.45 (m, 1H), 5.28 (s, 1H), 4.72 (m, 1H), 2.91 (m, 1H), 1.73 (m, 1H).

Provenance & Evidence