2-phenoxypropanenitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-phenoxypropionitrile (11.0 s.) in dry ether (50 ml.) was added dropwise to a stirred suspension of lithium aluminium hydride (3.8 g.) in dry ether (50 ml.). The mixture was then heated to reflux for 3 hours, cooled and treated cautiously (vigorous stirring) with water (3.8 ml.) then with 15% aqueous sodium hydroxide (3.8 ml.) and finally with water (11.4 ml.). The mixture was stirred for 20 minutes and filtered. The filtrate was dried over anhydrous potassium carbonate and evaporated. The residue was distilled under water-pump vacuum to give pure 2-phenoxypropylamine, b.p. 115°-116°/15 mm. The mixture was then heated to reflux for 3 hours cooled treated cautiously filtered The filtrate was dried over anhydrous potassium carbonate evaporated The residue was distilled under water-pump vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of phenol (18.8 g.) and anhydrous potassium carbonate (25 g.) in dry ethyl methyl ketone (35 ml.) was stirred and heated to reflux, during the dropwise addition of a solution of 2-chloropropionitrile (19.7 g.) in dry ethyl methyl ketone (15 ml.) containing finely-powdered potassium iodide (0.5 g.). The addition took 20 minutes. Stirring and heating were continued for a total of 2 hours after which the mixture was cooled, poured into water (200 ml.) and extracted with ether (200, 75 and 75 ml.). The combined ether extract was washed several times with 2N-sodium hydroxide to remove phenol, dried over anhydrous sodium sulphate, and evaporated. The residue was distilled under water-pump vacuum to give pure 2-phenoxypropionitrile, b.p. 117°-118°/13 mm. heated The addition Stirring heating were continued for a total of 2 hours was cooled extracted with ether (200, 75 and 75 ml.) The combined ether extract was washed several times with 2N-sodium hydroxide to remove phenol dried over anhydrous sodium sulphate evaporated The residue was distilled under water-pump vacuum