Hydrochloric Acid → HCID 12339646, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-cyano-benzyloxy)-acetic acid ethyl ester (J. Org. Chem. 1985, 50, 2128) (30 g, 136 mmol) and KOH (38 g, 680 mmol) in 1:1 EtOH/H2O (270 ml) was heated to 90° C. (oil bath) for 15 h. After cooling to room temperature the mixture was treated with conc. HCl until the pH=1 and extracted with CH2Cl2. The combined organic layers were dried concentrated in vacuo to yield an orange oil. The oil was dissolved in aq. Na2CO3, treated with activated carbon, filtered and the pH adjusted to 1 with conc. HCl. The resulting solid was collected by filtration and dried to yield 8.2 g of 2-[(carboxymethoxy)methyl]benzoic acid as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ 12.9 (bs, 1H), 7.87 (dd, J=7.77, 1.14 Hz, 1H), 7.66 (m, 1H), 7.59 (m, 1H), 7.39 (m, 1H), 4.90 (s, 2H), 4.15 (m, 2H).

Provenance & Evidence