Hydrochloric Acid → 3-Chloro-2-hydroxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

3-Chloro-2-hydroxybenzoylchloride (8.7 mmol) was dissolved in diglyme (10 ml) and cooled to -70° C. under argon. Lithium tritertbutoxyaluminohydride (0.5M, 34.8 ml 17.4 mmol) was added via syringe keeping the temperature below -60° C. The reaction was stirred at -60° C. for 2% hours. The reaction mixture was poured onto ice, acidified with concentrated HCl and extracted with ethyl acetate (2×). The organic phases were combined, dried over MgSO4 and evaporated. Flash chromatography (eluant: CH2Cl2 /hexanes) gave the title product (0.2 g, 1.3 mmol). MS (CI+) (M+NH4)+ 174

Provenance & Evidence