2-Chloroethanol → 2-Chloroethyl 3-hydroxybenzoate

Participants

Reaction Steps

A solution of 3-hydroxybenzoic acid (15.0 g, 0.11 mol) in 2-chloroethanol (70 mL, 1.0 mol) and 1 mL of concentrated sulfuric acid was refluxed for overnight. TLC analysis (silica gel/20% ethyl acetate/hexane) showed clean conversion to a new material. The excess chloroethanol was removed by evaporation to obtain a brown solution which was dissolved in ethyl acetate and washed with water. The organic layer was dried with MgSO4 and concentrated to obtain 21.0 g of the product as a white solid: mp 50° C.; 1H NMR (CDCl3) δ3.81 (t, 2H, J=5.9 MHz), 4.57 (t, 2H, J=5.9 MHz), 4.77 (s, 1H), 7.06-7.66 (m, 4H); 13C NMR (CDCl3) δ41.52, 64.75, 116.43, 120.77, 121.98, 129.80, 130.71, 156.04, 166.57; MS m/e (rel intensity) 200 (26), 138 (59), 121 (100), 93 ( 31), 65 (21), 39 (12); Exact mass: calcd 200.0240, found 200.0242. ##STR27##

Provenance & Evidence