Sodium Hydroxide → HCID 59726065, compound

Participants

Reaction Steps

To a stirred solution of aniline 2-3 (11.5 g, 460 mmol) in methanol (250 mL) and H2O (70 mL) was added 2N NaOH (25 mL). The reaction mixture was heated under reflux for 1 h, more 2N NaOH (25 mL) was added and the mixture was heated under reflux for a further 1 h. The solution was cooled and methanol was removed in vacuo. The mixture was dissolved in H2O and extracted with ethyl acetate. The aqueous layer was acidified to pH 2 with conc. HCl. and then extracted into ethyl acetate (×3). The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated to provide the acid 2-4 as a beige solid (10.4 g, 95% yield). 1H NMR (MeOD, 400 MHz) δ 3.80 (s, 3H), 6.70 (s, 1H).

Provenance & Evidence