Water → HCID 11008421, compound

Participants

Reaction Steps

[[(3-Chlorocyclobutyl)methoxy]methyl]benzene (82 g, 0.39 mole) in 390 ml of dry dimethylsulfoxide was slowly added to a solution of potassium t-butoxide (132 g, 1.17 mole) in 390 ml of dry dimethylsulfoxide in a water-bath at 18° C. under a dry argon atmosphere. After stirring for 1 hour at room temperature, the reaction mixture was poured into 1600 ml of water and extracted with ether (3×1000 ml). The ether extracts were back-extracted with water (4×2000 ml) and the ether extract was then dried over sodium sulfate. The ether was removed in vacuo and the crude product was purified on a Merck silica column, eluting the column with 5% ethyl acetate-hexane. Appropriate fractions were combined and the solvents removed in vacuo yielding 60.0 g of the title compound as a colorless liquid.

Provenance & Evidence