Methanol → HCID 85701783, compound

Participants

Reaction Steps

Cool a solution of 3-hydroxy-2-propyl-benzoic acid (59.79 g, 332 mmol) in MeOH (598 mL) to −10° C. and add thionyl chloride (36.26 mL, 497.1 mmol) using a syringe pump over 35 min. Allow the mixture to warm to ambient temperature while stirring over 35 h. Concentrate the mixture in vacuo and dilute the residue with methyl-tert-butylether (360 mL). Concentrate the resultant mixture in vacuo to dryness to yield the title compound (64.4 g, 87%) as a tan solid. 1H NMR (300 MHz, CDCl3) δ 7.38 (dd, J=8.0, 0.8 Hz, 1H); 7.10 (t, J=8.0 Hz, 1H); 6.93 (dd, J=8.0, 0.8 Hz, 1H); 5.1 (bs, 1 H); 3.89 (s, 3H); 2.98 (m, 2H), 1.61 (m, 2H); 1.00 (t, J=7.4 Hz, 3H).

Provenance & Evidence