Water → 4-[2-(p-Pentylphenyl)ethenyl]cyclohexanecarbonitrile

Temperature

0 °C

A mixture of 2.51 g of (p-pentylphenyl)methyl-triphenylphosphonium bromide and 615 mg of 4-cyanocyclohexanecarboxaldehyde (cis/trans mixture about 1:1) in 30 ml of t-butyl methyl ether was placed at 0° C. in a sulphonation flask while gassing with argon, the mixture was treated within 2 minutes with 673 mg of solid potassium t-butylate and the mixture was subsequently stirred at 0° C. for a further 1.5 hours. The red-brown, heterogeneous mixture was then poured into 100 ml of water and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed twice with 50 ml of water each time and once with 50 ml of saturated sodium chloride solution, dried over magnesium sulphate and concentrated. The residue was suspended in 150 ml of hexane, freed from precipitated triphenylphosphine oxide by filtration (back-washing with hexane) and the filtrate was concentrated. Low-pressure chromatography (0.4 bar) of the resulting oil (1.36 g) on silica gel with 3% ethyl acetate/petroleum ether as the eluant gave 1.02 g (81%) of 4-[2-(p-pentylphenyl)ethenyl]cyclohexanecarbonitrile as a colourless oil; Rf values of this isomer mixture (10% ethyl acetate/petroleum ether): 0.27 and 0.36.

1. customwas placed at 0° C. in a sulphonation flask
2. extractionextracted three times with 100 ml of diethyl ether each time
3. washThe organic phases were washed twice with 50 ml of water each time
4. dry with materialonce with 50 ml of saturated sodium chloride solution, dried over magnesium sulphate
5. concentrationconcentrated
6. customfrom precipitated triphenylphosphine oxide
7. filtrationby filtration (back-washing with hexane)
8. concentrationthe filtrate was concentrated

ORD record

ord-00c8a2be896d449e9ebd1fb52be91023

Source dataset

uspto-grants-1988_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04783280