Lithium Hydroxide → 4-(3-Bromophenoxy)butanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-(3-bromophenoxy)butanoate (Preparation 55A, 3.3 g, 11.5 mmol) in THF (5 mL) was added lithium hydroxide (0.550 g, 23.0 mmol) dissolved in water (5 mL) at room temperature. The reaction mixture was heated at 50° C. for 3 h. The reaction mixture was concentrated and partitioned between ethyl acetate (50 mL) and 1N aqueous hydrochloric acid (20 mL) (pH of aqueous layer ˜3). The organic layer was washed with brine (20 mL), dried over sodium sulfate, and concentrated under reduced pressure to yield 4-(3-bromophenoxy)butanoic acid (2.9 g, 11.2 mmol, 97% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.10-2.15 (m, 2H), 2.59 (t, J=7.26 Hz, 2H), 4.01 (t, J=6.05 Hz, 2H), 6.82 (ddd, J=8.14, 2.42, 1.10 Hz, 1H), 7.04-7.06 (m, 1H), 7.07-7.10 (m, 1H), and 7.14 (t, J=8.03 Hz, 1H).

Provenance & Evidence