p-Toluenesulfonic acid → HCID 20468638, compound

Participants

Reaction Steps

A mixture of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid (5.6 g, 0.015 mole), 2-hydroxyethyl ether (6.4 g, 0.06 mole) and p-toluenesulfonic acid (200 mg) was heated at 135°-142° C. for 26 hrs. The resulting solution was cooled to room temperature, taken into 400 ml of ether. The ethereal solution was washed three times with water, dried over CaSO4 and concentrated to 4.9 g of a yellowish gum. The gum was chromatographed on silica gel and eluted with hexane-ethyl acetate (90:10); yield 3.4 g of pure 5-hydroxy-3-oxapentyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate as a pale yellow gum; nmr (DMSO-d6) δ 3.56 (s, broad 5H), 3.76 (m, 2H), 4.52 (m, 2H), 7.18-8.40 (m, 6H); ir (CHCl3) 3610, 1750 Cm-1.

Provenance & Evidence