m-Chloroperbenzoic acid → 2,2-Dinitropropyl glycidyl ether

Participants

Reaction Conditions

Reaction Steps

A solution of allyl 2,2-dinitropropyl ether (30 g, 160 mmol) in chloroform (50 ml) was added to a mechanically stirred mixture of m-chloroperoxybenzoic acid (35 g, 200 mmol) and chloroform (300 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 yellow liquid residue (31 g) was chrornatographed using silica gel and methylene chloride to give 21 g (63% yield) of 2,2-dinitropropyl glycidyl ether: HNMR (CDCl3): 2.19 (s, 3H), 2.57 (d of d, 1H), 2.79 (t, 1H), 3.10 (m, 1H), 3.40 (d of d, 1H), 3.91 (d of d, 1H), 4.35 (AB quartet, 2H) ppm; IR (neat): 3063 (w), 3005 (m), 2927 (m), 1566 (br, vs), 1468 (m), 1443 (m), 1402 (m), 1380 (m), 1329 (s), 1280 (w), 1254 (w), 1232 (w), 1161 (m), 1112 (br, s), 999 (w), 967 (w), 905 (m), 849 (m), 764 (m) cm−1.

Provenance & Evidence