Sodium Hydroxide → HCID 18401029, compound

Participants

Reaction Steps

To the crude reaction mixture described in example 3 containing acetic acid 2-[5-methoxy-2-(2,2,2-trifluoro-1-hydroxy-1-methyl-ethyl)-phenyl]-ethyl ester was added 1N aqueous sodium hydroxide (75.0 mL, 75 mmol). The reaction mixture was allowed to warm to room temperature and was stirred 12 hours. The reaction mixture was poured into water (75 mL) and extracted with methyl tert-butyl ether (150 mL). The organic layer was washed with water (75 mL) and brine (75 mL), dried over magnesium sulfate, and concentrated to an oil. To the crude oil was added hexanes (20 mL) and methyl tert-butyl ether (4 mL) and a solid precipitated. The mixture was stirred for 30 minutes and filtered to provide 1,1,1-trifluoro-2-[2-(2-hydroxy-ethyl)-4-methoxy-phenyl]-propan-2-ol (7.3 g, 52% overall yield from acetic acid 2-(2-acetyl-5-methoxy-phenyl)-ethyl ester). M.p. 110-111° C. 1H NMR (300 MHz, CDCl3) δ1.83 (s, 3), 2.91 (dt, 1, J=13.7, 3.9), 3.76 (ddd, 1, J=13.7, 9.3, 4.4), 3.85 (s, 3), 3.85-3.93 (m, 1), 4.08 (dt, 1, J 9.3, 3.7), 6.80-6.83 (m, 2), 7.38 (d, 1, J=8.4). 13C NMR (100 MHz, CDCl3) δ26.01, 36.12, 55.19, 64.13, 76.52 (q, J=28.9), 111.47, 117.43, 125.99 (q, J=287), 129.69, 129.94, 140.86, 159.55. IR 3395, 3162, 1610, 1513, 1467, 1248, 1157, 1087, 1046 cm−1. Analysis calculated for C12H15F3O3: C, 54.54; H, 5.72. Found: C, 54.65; H, 5.70.

Provenance & Evidence