Chloroacetic Acid → Naphthoxyacetic acid

Participants

Reaction Steps

To a solution of potassium hydroxide (2.98 g, 52.1 mmol) in H2O (35 mL) was added 1-naphthol (3.08 g, 21.4 mmol), followed by 2-chloroacetic acid (2.32 g, 24.7 mmol). The resulting mixture was heated at reflux for 3 h, then allowed to cool and extracted with EtOAc. The aqueous phase was made acidic by the addition of 3N HCl and extracted with EtOAc. The organic phase from the acidic extraction was washed with saturated aqueous NaCl. The solvent was removed in vacuo to provide the title compound (2.78 g, 64%).

Provenance & Evidence