Diethyl Ether → cis-4-(2-Tridecenyloxymethyl)phenylmethanol

Participants

Reaction Steps

To a solution of silyl ether (41) (341 mg, 0.84 mmol) in CH3CN (10 mL) was added 50% aqueous HF (1 mL) the mixture was stirred at room temperature for 15 minutes. The reaction mixture was poured into saturated aqueous NaHCO3 (50 mL) and ether (75 mL). The organic layer was separated and washed with two 50-mL portions of water, dried (MgSO4), and concentrated to yield (42) (290 mg, 98%) as a colorless oil: Rf 0.24 (9:1 petroleum ether/EtOAc); 1H NMR (CDCl3) δ 7.30 (s, 4 H), 5.60 (m, 2 H), 4.63 (s, 2 H), 4.49 (s, 2 H), 4.07 (d, J=5.1 Hz, 2 H), 239 (s, 2 H), 2.04 (q, J=6.6 Hz, 2 H), 1.27 (m, 16 H), 0.89 (t, J 6.6 Hz, 2 H); 13C NMR (CDCl3) δ 140.49, 137.82, 134.24, 128.10, 127.12, 125.94, 71.88, 65.85, 65.03, 32.03, 29.76, 29.66, 29.48, 29.37, 27.73, 22.82, 14.24. ##STR9##

Provenance & Evidence