Allyl bromide → Cyclohexanone, 2-(2-propen-1-yl)-

Participants

Reaction Conditions

Reaction Steps

A suspension of potassium t-butoxide (200 g, 1.78 mol) in toluene which was cooled to 0° C. in an ice bath under N2 was treated with cyclohexanone (157 g, 1.60 mol). To the reaction mixture was slowly added allyl bromide (194 g, 1.60 mol) over a 2 hour period. The reaction was warmed to room temperature over 5 hours. The reaction was then poured into EtOAc (400 mL) and washed once with 10% potassium hydrogen sulfate (250 mL). The organic solution was then washed with brine (3×200 mL), dried over magnesium sulfate, and evaporated under reduced pressure. The resulting oil was then chromatographed to yield 158.4 g (71.6%) of 2-allyl cyclohexanone as an oil. 1H NMR (CDCl3, 300 MHz) d 1.2-2.5 (m, 10H), 2.59 (m, 1H), 5.0 (dd, 2H), 5.75 (m, 1H). 13C NMR (CDCl3, 75 MHz) d 25.04, 28.03, 33.46, 33.86, 42.12, 50.35, 116.3, 136.6, 212.5.

Provenance & Evidence