m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

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).

1. filtrationThe precipitate is filtered off with suction
2. filtrationfiltered off with suction again
3. dissolutionThe solid residue is dissolved in 2N HCl
4. extractionthe acid aqueous solution is extracted several times
5. stirringby shaking with diethyl ether
6. concentrationfinally concentrated completely
7. extractionThe residue is extracted with hot ethanol in several portions
8. concentrationThe ethanol extracts are concentrated
9. customthe residue is dried

ORD record

ord-99796af2dfb442b4987e3d94f8747a1f

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05631259