Phosphorus oxychloride → HCID 368833, compound

Participants

Reaction Steps

A solution of the acid 33 (0.5 g, 1.4 mmol) in phosphorous oxychloride (5 mL, 53.4 mmol) was heated at reflux for 3 min. The dark red solution was poured onto crushed ice (about 30 g) and extracted with ether (50, 20, and 20 mL). The combined ether layer was dried over anhydrous sodium sulfate. Evaporation of the filtrate gave a gray solid. Recrystallization of this gray solid from ethyl acetate and hexane afforded pale gray crystals 0.32 g (69.6%): mp 104°-106° C.; IR (KBr) 3010, 2960, 1697, 1595, 1512, 1323, 1251, 1139 cm-1 ; 1H NMR (CDCl3, 200 MHz) δ7.11 (d, 2H, J=8 Hz), 6.85 (d, 2H, J=8 Hz), 6.71 (s, 1H), 4.03 (s, 3H), 3.96 (s, 3H), 3.87 (s, 3H), 3.78 (s, 3H), 3.78 (m, 1H), 3.54 (m, 1 H), 3.10 (m, 1H); EIMS m/e 328 (M+, 98). Anal. (C19H20O5), C, H.

Provenance & Evidence