Acetyl chloride → HCID 18401031, compound

Participants

Reaction Steps

To a solution of aluminum tribromide (57.6 g, 216 mmol) in dichloromethane (90 mL) at 0° C. was slowly added acetyl chloride (11.5 mL, 162 mmol). To the reaction mixture was added (3-methoxy-phenyl)-acetic acid (17.9 g, 108 mmol) in dichloromethane (20.0 mL). The reaction mixture was stirred for one hour and then poured over ice (100 mL). The organic layer was separated and 1N aqueous sodium hydroxide was added (100 mL). The biphasic mixture was stirred vigorously for 90 minutes and the layers were separated. The organic layer was discarded and concentrated hydrochloric acid was added to the aqueous layer until the pH reached 1. A solid precipitated and was filtered and air-dried to afford (2-acetyl-5-methoxy-phenyl)-acetic acid (16.8 g, 75%). M.p. 153-155° C. 1H NMR (300 MHz, CDCl3) δ2.68 (s, 3), 3.91 (s, 3), 3.92 (s, 2), 6.92-6.95 (m, 2), 7.88 (d, 1, J=9.5). 13C NMR (100 MHz, CDCl3) δ28.33, 41.43, 55.46, 112.54, 118.26, 129.17, 133.08, 136.94, 162.65, 174.80, 200.96. IR 3435, 1704, 1663, 1609, 1568, 1258 cm−1. Analysis calculated for C11H12O4: C, 63.45; H, 5.81. Found: C, 63.35; H, 5.46.

Provenance & Evidence