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 combined ether extracts were back-extracted with water (4×2000 ml), the extracts were then dried over sodium sulfate, and the volatiles were removed in vacuo. The crude product was divided into two equal portions and each portion was purified on separate 3.5 liter Merck silica columns, eluting with 3% 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