1-(4-Chlorophenyl)-1-cyclopropyl-2-propen-1-ol → HCID 57191402, compound

Participants

Reaction Steps

To a stirred solution of 51.3 grams (0.192 mole) of pyridinium chlorochromate in 210 mL of methylene chloride was added in one portion a solution of 20.0 grams (0.096 mole) of 1-cyclopropyl-1-(4-chlorophenyl)-2-propen-1-ol in 25 mL of methylene chloride. Upon completion of addition the reaction mixture was stirred at ambient temperature for two hours. The supernatent liquid was decanted from a residue, and the residue was extracted with diethyl ether. The decantate and the extract were combined and were washed in turn with two 100 mL portions of aqueous 5% hydrochloric acid, and a 50 mL portion of an aqueous solution saturated with sodium bicarbonate. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel using 5% diethyl ether in hexane as the eluant. The appropriate fractions were combined and concentrated under reduced pressure yielding 6.8 grams of 3-cyclopropyl-3-(4-chlorophenyl)propenal.

Provenance & Evidence