Cyclohexene → 1-(4-Phenylcyclohexyl)-1-propanone

Temperature

-60 °C

In a 2,000 mL (inside volume) three-necked flask equipped with a reflux condenser, 600 mL of hexane and 160 g of anhydrous AlCl3 were mixed and cooled to −60° C., to which were then added 110 g of propionyl chloride and 82.2 g of cyclohexene. The temperature of the mixture was raised to −40° C. while stirring the mixture for 3.5 h. The solvent was then removed by decantation and the residues were washed with cold hexane. The thus obtained 1-propionyl-2-chlorocyclohexane was added with 500 mL of benzene and an additional amount (60 g) of AlCl3. The mixture was then stirred at 45° C. for 3.5 h. The reaction liquid was cooled to room temperature and then poured onto ice. An oil layer was separated and concentrated to obtain 130 g of (4-propionylcyclohexyl)benzene. This was mixed with 1,200 mL of diethylene glycol, 225 g of potassium hydroxide and 310 g of 80% by mass hydrazine hydrate. After refluxing the resulting mixture for 1 h, the contents in the flask were heated to 220° C. to distil off volatile matters therefrom. The mixture was further refluxed for 1 h, cooled to room temperature and then poured in water. An oil layer was then extracted with hexane, washed with water, 5% by mass sulfuric acid and 80% by mass sulfuric acid and then dried. The obtained oil layer was purified by distillation to obtain 85 g of (4-n-propylcyclohexyl)-benzene. As a result of gas chromatography, it was confirmed that the (4-n-propylcyclohexyl)benzene purity was 98.0% and the cis/trans molar ratio was 1.36.

1. customIn a 2,000 mL (inside volume) three-necked flask equipped with a reflux condenser
2. temperatureThe temperature of the mixture was raised to −40° C.
3. customThe solvent was then removed by decantation
4. washthe residues were washed with cold hexane
5. additionThe thus obtained 1-propionyl-2-chlorocyclohexane was added with 500 mL of benzene
6. stirringThe mixture was then stirred at 45° C. for 3.5 h
7. customThe reaction liquid
8. temperaturewas cooled to room temperature
9. additionpoured onto ice
10. customAn oil layer was separated
11. concentrationconcentrated

ORD record

ord-786f62e6435f44378bca5d1e63c9e313

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07777081B2