Ethanol → 2-Phenylacrylonitrile

Phenylacetonitrile (117 g, 1.0 mol), 37% formaldehyde solution 85 g, 1.0 mole of formaldehyde), ethanol (100 ml), and 40% benzyltrimethylammonium hydroxide (Triton B) (2 ml) were mixed in a 500 ml 3-necked round-bottomed glass flask equipped with a magnetic stirrer, water-cooled condenser and thermometer. A static atmosphere of argon was maintained throughout the course of the reaction. The reaction mixture was mixed and heated to reflux temperature whereupon the heat of reaction was sufficient to maintain the reaction without external heating. After ten minutes the mixture had formed two layers. It was cooled and the top layer containing mostly alcohol and water was separated. The lower viscous yellow layer was dissolved in acetone and charged to a distillation flask together with 0.1 g hydroquinone. Distillation under reduced pressure yielded 30 g of a water-white distillate boiling at 95°-100°/1.0 mm Hg (23 percent of theory). 1H NMR: (CDCl3, TMS), δ7.0 (S, 5H), 6.1, 5.85 (s, s, 2 H).

1. customequipped with a magnetic stirrer
2. temperatureA static atmosphere of argon was maintained throughout the course of the reaction
3. additionThe reaction mixture was mixed
4. temperatureheated
5. temperatureto reflux temperature whereupon the
6. temperatureheat of reaction
7. temperatureto maintain
8. customthe reaction without external heating
9. customAfter ten minutes the mixture had formed two layers
10. temperatureIt was cooled
11. customwas separated
12. dissolutionThe lower viscous yellow layer was dissolved in acetone
13. additioncharged to a distillation flask together with 0.1 g hydroquinone
14. distillationDistillation under reduced pressure
15. customyielded 30 g of a water-white distillate boiling at 95°-100°/1.0 mm Hg (23 percent of theory)

ORD record

ord-d570d7b274464044bf89562de26319a0

Source dataset

uspto-grants-1982_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04366170