Chloroacetic Acid → 2-Naphthoxyacetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of potassium hydroxide (10.0 g, 0.175 mol) in H2O (100 mL) was added 2-naphthol (10.43 g, 72 mmol), followed by 2-chloroacetic acid (7.79 g, 83 mmol). The resulting mixture was heated at 70° C. for 4 h, then allowed to cool. The mixture was filtered, and the filtrate was 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 successively with H2O and saturated aqueous NaCl. The solvent was removed in vacuo to provide the title compound (2.11 g, 14%).

Provenance & Evidence