Isopropanol → 1-Isopropoxycyclohexene

Temperature

5 °C

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%.

1. customwas placed in a three-neck round bottom flask
2. customrose to about 15-20° C.
3. stirringThe mixture was stirred at 20° C. until gas-chromatographic (“GC”) analysis
4. customcompletion of the reaction
5. customThe by-products isopropyl formate and isopropanol were removed by distillation under reduced pressure
6. distillationThe remaining residue was subsequently distilled

ORD record

ord-8fe0e5a4ca284a75be776bb6640a2d22

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235944B1