m-Chloroperbenzoic acid → HCID 86761714, compound

Participants

Reaction Conditions

Reaction Steps

A solution of allyl trinitroethyl ether (111 g, 502 mmol) in chloroform (100 ml) was added to the mechanically stirred mixture of m-chloroperoxybenzoic acid (102 g, 590 mmol) and chloroform (450 ml). The mixture was refluxed at 70° C. for 6 h under nitrogen. The mixture was cooled with an ice bath for 30 min and filtered. The filtrate was concentrated and additional precipitate was filtered out. The filtrate was diluted with methylene chloride, washed with 10% sodium thiosulfate, saturated sodium bicarbonate, water and dried. Solvent was removed under vacuum. The golden yellow liquid residue (109 g) was chromatographed in portions using silica gel and methylene chloride to give 72 g (60% yield) of glycidyl trinitroethyl ether: 1HNMR (CDCl3) 2.64 (d of d, 1H), 2.87 (t, 1H), 3.22 (m, 1H), 3.53 (d of d, 1H), 4.15 (d of d, 1H), 4.85 (AB quartet, 2H) ppm; IR (neat): 3067 (w), 3006 (m), 2932 (m), 1591 (br, vs), 1454 (m), 1340 (m), 1305 (s), 1254 (m), 1161 (m), 1138 (s), 1082 (m), 1032 (w), 988 (w), 945 (w), 900 (m), 880 (m), 855 (m), 804 (s), 782 (m) cm−1.

Provenance & Evidence