Citric Acid → 4-Allyloxy-2,3-dihydroxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

Tin tetrachloride (0.31 g, 0.14 mL, 1.32 mmol) was added to a solution of 39 (0.20 g, 1.20 mmol) and αα′-dichloromethyl methyl ether (0.15 g, 0.12 mL, 1.32 mmol) in CH2Cl2 at −78° C. The pale brown reaction mixture was stirred at this temperature for 1.5 h, then poured into an excess of saturated NaHCO3 aq. cooled at 0° C. The mixture was stirred for 15 min, acidified to pH 5 by the addition of 5% w/v citric acid then extracted with CH2Cl2 (3×). The organic phase was dried (Na2SO4) and evaporated to dryness to give 40 compound (0.18 g, 76%) which was used as such in the next step.

Provenance & Evidence