Sodium Hydroxide → 5-(3-methoxyphenyl)pentanoic Acid

Participants

Reaction Steps

A mixture of ethyl 5-(3-methoxyphenyl)pentanoate (1 equivalent) and sodium hydroxide (3 equivalents) in THF/H2O was heated at reflux overnight. THF was evaporated, the aqueous phase acidified with 6N HCl to pH<5, and then extracted with a mixture of chloroform:isopropyl alcohol (3:1, 5 times). The organic phase was dried over anhydrous sodium sulfate. A light yellow oil was obtained in more than 85% yield after removal of the solvent: 1H NMR δ 7.20 (m, 1H), 6.79-6.73 (m, 3H), 3.80 (s, 3H), 2.62 (m, 2H), 2.38 (m, 2H), 1.68 (m, 4H).

Provenance & Evidence