Isopropanol → 1-Isopropoxycyclohexene

Temperature

60 °C

To a mixture at room temperature containing 196.32 grams (2 mol) of cyclohexanone, 390.4 grams (2.06 mol) of triisopropyl orthoformate and 12.00 grams of isopropanol (0.2 mol), was added 7.6 grams (0.055 mol) of sodium hydrogensulfate monohydrate. The reaction was exothermic and upon addition of the catalyst, the temperature of the reaction mixture rose to 35° C., and was heated and maintained at 60° C. for 1 hour. The progress of the reaction was monitored by GC until the cyclohexanone content dropped to less than 2%. The isopropanol and isopropyl formate were distilled off under reduced pressure until the reaction mixture's temperature reached a maximum of 100° C. The reaction mixture was cooled to room temperature and filtered to remove sodium hydrogensulfate monohydrate (recovered). The pH value of the filtrate was adjusted to about 7˜8 by adding 0.8 gram of potassium iso-propoxide. The mixture was then heated under reduced pressure to remove unreacted cyclohexanone. The product, 1-isopropoxy-1-cyclohexene was isolated by distillation as a clear liquid; the yield was 81.7% with a purity exceeding 98%.

1. additionThe reaction was exothermic and upon addition of the catalyst
2. customrose to 35° C.
3. temperaturewas heated
4. additiondropped to less than 2%
5. distillationThe isopropanol and isopropyl formate were distilled off under reduced pressure until the reaction mixture's temperature
6. customa maximum of 100° C
7. temperatureThe reaction mixture was cooled to room temperature
8. filtrationfiltered
9. customto remove sodium hydrogensulfate monohydrate (recovered)
10. additionby adding 0.8 gram of potassium iso-propoxide
11. temperatureThe mixture was then heated under reduced pressure
12. customto remove unreacted cyclohexanone

ORD record

ord-d286ee6461874790a52c5b142e85ede8

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235944B1