Water → Benzonitrile, 4-(4-pentenyl)-

A suspension of 6.5 g of methyl-triphenylphosphonium bromide in 50 ml of t-butyl methyl ether was treated with 2.1 g of potassium t-butylate at -5° C. and the mixture was then stirred at room temperature for 40 minutes. Subsequently, the mixture was treated at 0° C. with a solution of 2.6 g of 4-(p-cyanophenyl)butyraldehyde in 30 ml of t-butyl methyl ether and the resulting mixture was stirred for 1 hour at room temperature. Thereafter, the reaction mixture was treated with water and extracted three times with diethyl ether. The organic phases were washed twice with water, dried over magnesium sulphate, filtered and concentrated. The crystalline residue was dissolved in hot ethyl acetate, the solution was treated with petroleum ether and the precipitated triphenylphosphine was filtered off. The oil obtained after concentrating the filtrate was purified by chromatography on silica gel with ethyl acetate/petroleum ether (vol. 5:95), whereby 1.92 g of p-(4-pentenyl)benzonitrile were isolated as a light yellowish liquid.

1. stirringthe resulting mixture was stirred for 1 hour at room temperature
2. extractionextracted three times with diethyl ether
3. washThe organic phases were washed twice with water
4. dry with materialdried over magnesium sulphate
5. filtrationfiltered
6. concentrationconcentrated
7. dissolutionThe crystalline residue was dissolved in hot ethyl acetate
8. additionthe solution was treated with petroleum ether
9. filtrationthe precipitated triphenylphosphine was filtered off
10. customThe oil obtained
11. concentrationafter concentrating the filtrate
12. customwas purified by chromatography on silica gel with ethyl acetate/petroleum ether (vol. 5:95)

ORD record

ord-50e7604eca9e466dbc974483f3420397

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05238602