Diethyl Ether → 3-m-Anisyl-1-propanol

Participants

Reaction Steps

A magnetically stirred solution of 3-(3-methoxyphenyl)propionic acid (71.38 g, 396.0 mmol) in 1.00 L of anhydrous tetrahydrofuran (THF) at room temperature was treated dropwise with a solution of borane-dimethyl sulfide (2.0M in THF, 680 mmol), stirred 1 h, heated at reflux for 2 h, cooled to room temperature, and stirred 12 h. The solution was poured over ice (300 g), treated with 6N NaOH (500 mL), and stirred 1 h. The suspension was treated with diethyl ether (500 mL), the layers were separated, and the aqueous layer extracted with fresh diethyl ether (2×400 mL). The combined organic extracts were washed with water (500 mL), saturated sodium chloride solution (2×500 mL), dried (K2CO3), filtered, and concentrated in vacuo to give a clear liquid. Kugelrohr distillation (0.1 torr, 120° C.) gave 63.89 g (97%) of the alcohol: 1H NMR (CDCl3) δ 7.21 (t, J=8 Hz, 1 H), 6.81-6.72 (m, 3 H), 3.80 (s, 3 H), 3.68 (t, J=7 Hz, 2 H), 2.68 (t, J=8 Hz, 2 H), 1.95-1.85 (m, 2H), 1.40 (bs, 1 H).

Provenance & Evidence