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

Temperature

0 °C

A mixture of 2.51 g of (p-pentylphenyl)methyl-tri-phenylphosphonium bromide and 615 mg of 4-cyanocyclohexanecarboxaldehyde (cis/trans mixture about 1:1) in 30 ml of t-butyl methyl ether at 0° C. was placed in a sulphonation flask under argon gasification, treated within 2 minutes with 673 mg of solid potassium t-butylate and subsequently stirred at 0° C. for a further 1.5 hours. Then, the red-brown heterogeneous mixture was 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 (rinsing 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 in a sulphonation flask under argon
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 (rinsing with hexane)
8. concentrationthe filtrate was concentrated

ORD record

ord-b121007fcd5e4c5cab2004aad593c769

Source dataset

uspto-grants-1987_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04708441