Water → 2,4-Dinitrobenzyl mercaptan

Participants

Reaction Steps

A stirred suspension of S-(2,4-dinitrobenzyl) thioacetate 16b (8.2 g, 32 mmol) in concentrated sulfuric acid--water (1:1 v/v; 14.08 cm3) and methanol (128 cm3) was heated, under reflux, for 1.5 h. The cooled products were poured into water (300 cm3) and the resulting mixture was extracted with ether (2×400 cm3). The combined organic extracts were washed with water (300 cm3), dried (MgSO4) and evaporated under reduced pressure to give 2,4-dinitrobenzyl mercaptan 17b as a yellow oil (6.75 g, 98 %) (Found: M+ =214.0084 12 C11H614N216O432S requires: 214.0048); δH [CDCl3 ] 2.21 (1 H, t, J 8.7), 4.10 (2 H, d, J 8.7), 7.75 (1 H, d, J 8.7), 8.44 (1 H, dd, J 2.4 and 8.5), 8.77 (1 H, d, J 2.4); δC [CDCl3 ] 26.2, 121.0, 127.8, 133.0, 143.6, 146.9, 148.0.

Provenance & Evidence