Hydrochloric Acid → 2,3-Dihydroxy-1-naphthaldehyde

Participants

Reaction Conditions

Reaction Steps

A stream of HCl gas was passed through a stirred, cooled (0° C.) mixture of 2,3-dihydroxynaphthalene (6 g, 37.4 mmol) and zinc cyanide (6.6 g, 56.1 mmol) in dry Et2O (28 mL) for 20 min. An insoluble yellow oil was generated. Stirring was continued for 1 h at 0° C., then at room temperature for 1 h. The yellow brown oil was separated and washed with Et2O. Water (120 mL) was added and the mixture was heated at 60° C. for 10 min. The yellow solid generated was filtered and washed with water to give product (5.48 g, containing 20% starting material). MS (APCI) m/z 187 (M−H).

Provenance & Evidence