HCID 15506059, compound → 2-(3-ethoxyphenyl)acetic acid

Participants

Reaction Steps

A solution of methyl 3-ethoxyphenylacetate (92.6 g, 0.4 mole) in methanol (600 ml) and 6.25N NaOH (400 ml) was stirred overnight at room temperature and then filtered and concentrated in vacuo to remove the methanol. The solution was adjusted to pH 1 with concentrated HCl, the resulting precipitate filtered, washed with ice water, and dried under high vacuum to give 3-ethoxyphenyl acetic acid (74.5 g). M.p=89°-90° C. 1H NMR (DMSO-d6, 200 MHz) δ: 1.30 (6, J=7 Hz, 3H, CH3), 3.50 (s, 2H, ArCH2), 3.98 (q, J=7 Hz, 2H, ethyl CH2), 6.75-6.80 (m, 3H, Ar), 7.14-7.23 (m, 1H, Ar). (Lit. ref.: J. Med. Chem, 1980, 23(4) 437-444.

Provenance & Evidence