Water → HCID 67708224, compound

Participants

Reaction Steps

A 10 mL solution of 1,1-dichloro-cis-2-(p-hydroxyphenyl)-3-phenylcyclopropane (Compound 9) (0.009 mol) and pyridine (0.79 g, 0.01 mol) in Et2O was heated under nitrogen to a gentle reflux, while acetyl chloride (0.78 g, 0.01 mol) was added dropwise slowly via a cannula. A white precipitate was noted immediately, and the mixture was refluxed for 1 h. The reaction flask was cooled while 5 mL of water was added dropwise. Et2O was used to extract the aqueous layer, and the combined Et2O layers were washed with 5% H2SO4, followed b a saturated NaHCO3 solution. Drying with anhydrous Na2SO4, and evaporation of ether gave a dark-yellow oil, which was chromatographed on a silica gel column and eluted with (3:1) CH2Cl2 /petroleum ether to provide a light-yellow oil (0.9 g, 31%). 1H NMR (CDCl3) δ 2.28 (s, 3H, OCOCH3), 3.30 (s, 2H, ArCH), 7.04 (s, 5H, ArH), 7.28 (m, 4H, ArH).

Provenance & Evidence