HCID 58697787, compound → HCID 58697786, compound

Participants

Reaction Steps

A solution of 3-[(S)-1-phenyl-2,2,2-trifluoroethoxy]-4-[(4-methoxyphenyl)methoxy]-benzaldehyde (2.08 g, 0.005 mol) in acetic acid (25 mL) was heated to 150□C. and stirred for 72 h. It was then cooled to room temperature and concentrated in vacuo. The residue was diluted with ethyl acetate (100 mL), and the organic solution washed with water (100 mL) and extracted with 1M sodium hydroxide (5×100 mL). The basic extracts were combined and acidified to pH 1 with concentrated HCl, then extracted with ethyl acetate (2×100 mL). The organic extracts were combined, dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel and elution with petroleum ether:ethyl acetate (6:1) gave the product as a colourless oil, which later crystallised to a white powder (1.14 g, 80%). RF (dichloromethane) 0.53. 1H NMR (CDCl3) □ 9.71 (s, 1H, O═C—H), 7.09 (d, 1H, J 8.3 Hz, ArH), 6.39 (s, 1H, OH), 5.50 (q, 1H, J 6.0 Hz, CHCF3).

Provenance & Evidence