Water → Bis(1,3-benzodioxol-5-yl)methanol

Participants

Reaction Steps

A solution of 4-bromo-1,2-(methylenedioxy)benzene (5.02 g, 2.5 mmol) in 100 mL of dry tetrahydrofuran is cooled to -78° C. n-Butyllithium (15.6 mL, 2.5 mmol) is added dropwise to the reaction. The white suspension is stirred for another hour. Piperonal (4.12 g, 2.4 mmol) in 20 mL of tetrahydrofuran is added. The reaction is warmed to room temperature and stirred overnight. Water (50 mL) is added to quench the reaction. Layers are separated and the aqueous phase is extracted with 3×40 mL of ethyl acetate. The combined organics are dried (magnesium sulfate) and filtered. Solvent is removed in vacuo and the residue is purified by silica gel chromatography eluting with 20% ethyl acetate-hexane to give 6.1 g (90%) of product as a white solid;

Provenance & Evidence