Sodium Hydroxide → (4-Methylpyridin-2-yl)acetic acid

Participants

Reaction Steps

(4-Methyl-pyridin-2-yl)-acetic acid ethyl ester (1.0 g)—prepared according to Chem. Parm. Bull 32 (12), 1984, 4866-4872—was dissolved in ethanol (30 ml) and treated with a 1M ethanolic NaOH solution (5.83 ml). The mixture was refluxed for 4 hours, cooled and evaporated in vacuo. The residue was dissolved in water (50 ml) and the pH was adjusted to 3.0 with 1M HCl. The solvent was evaporated and the residue was suspended in ethanol (150 ml) and filtered. The clear filtrate was evaporated to dryness and the residue was dried in vacuo to give a light yellow solid (1.0 g). NMR (DMSO-d6): 8.65 (d, 1H); 7.72 (s, 1H), 7.68 (d, 1H), 4.04 (s, 2H), 2.49 (s, 3H).

Provenance & Evidence