Acetonitrile → 2-Phenylbut-3-enenitrile

A mixture of vinylbenzyl chloride in acetonitrile (5.0 g, 0.033 mol, in 10 mL of ACN) was added to a mixture of potassium cyanide (1.5 ME, 0.0495 mol, 3.2 g), 18-Crown-6 ether (0.52 g) and acetonitrile (15 mL). The resulting mixture was stirred overnight at room temperature. TLC analysis (hexane:ethyl acetate, 8:2) indicated that the reaction had gone to completion. The reaction was worked up by adding water to the reaction mixture (50 mL) and extracting the product into ethyl acetate. The organic layer was washed twice with water followed by brine solution. The organic layer was dried on Na2SO4 and recovered under reduced pressure to obtain the required vinylbenzyl cyanide as a light brown coloured oil (4.2 g, 87.8%) which was used without further purification in the next step. 1H NMR (400 MHz, CDCl3) δ3.7 (s, 2H), δ 5.3 (d, 1H, ethylene —CH trans), δ5.8 (d, 1H, ethylene-CH cis), δ 6.7 (m, 1H), δ 7.3 (Ar 2H, dd), δ 7.4 (Ar 2H, dd).

1. extractionextracting the product into ethyl acetate
2. washThe organic layer was washed twice with water
3. customThe organic layer was dried on Na2SO4
4. customrecovered under reduced pressure

ORD record

ord-bf33e0c6f3284d42b1cfb4477d0a2fbe

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993697B2