Isopropanol → 1-Isopropoxycyclohexene

Participants

Reaction Conditions

Reaction Steps

A mixture of 190.3 g (1 mol) triisopropyl orthoformate, 98.15 g (1 mol) of cyclohexanone and 6.00 g (0.10 mol) of isopropanol was placed in a three-neck round bottom flask and cooled to about 5° C. in an ice bath. The mixture was stirred and 0.4 g (2 mmol) of reagent grade iron (III) chloride was added. Upon addition of the FeCl3 catalyst, the temperature of the mixture rose to about 15-20° C., indicating that the reaction was proceeding. The mixture was stirred at 20° C. until gas-chromatographic (“GC”) analysis indicated completion of the reaction. The by-products isopropyl formate and isopropanol were removed by distillation under reduced pressure. The remaining residue was subsequently distilled to provide 1-isopropoxy-1-cyclohexene (bp 34° C. @3 mm Hg) as a colorless liquid; the yield was 92% with a purity exceeding 99%.

Provenance & Evidence