Acetyl chloride → HCID 86662378, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of dimethoxymethane (26.4 mL, 30 mmol) and zinc bromide (0.180 g, 0.08 mmol) in dichloromethane (200 mL) was slowly added drop wise acetyl chloride (21.2 mL, 24 mmol) at 10° C. and the stirring was continued for 1 h at this temperature, then 3 hours at room temperature. The solution was cooled at 5° C. and 2,4,6-trihydroxybenzaldehyde (21.1 g, 30 mmol) was added portion wise followed by slow drop wise addition of a solution of DIPEA (83.2 mL, 4.8 eq.). The cloudy solution was stirred overnight, then DCM (200 mL) was added and after washing with NH4Cl saturated solution (300 mL) was dried over Na2SO4. Removal of the solvent and filtration over a small pad of silica gel eluting with cyclohexane/ethyl acetate 9/1 afforded the title compound (21 g, 65% yield).

Provenance & Evidence