Sodium amide → 4-Pentenoic acid

Participants

Reaction Steps

To a boiling solution of 2-(2-methylphenyl)-3-methylbutyronitrile (Herz W., J.Am.Chem.Soc. 80, 3139, 1958) (207.9 g) and 86% 3,3-diethoxypropylchloride (154 g) in anhydrous toluene (1250 ml) is dropped during about 50 minutes under stirring 107.7 g of a 50% toluenic sodium amide suspension (NaNH2 content 53.8 g) and the mixture is refluxed under continuous stirring for 6 hours. On subsequent cooling, the stirred mixture is diluted with water (300 ml), the toluenic portion is separated and the aqueous phase is extracted with toluene. The organic solutions are combined, washed with water and saturated brine (aqueous sodium chloride solution) until the reaction is neutral, and then it is dried over anhydrous sodium sulfate. Finally, the solvent is evaporated under reduced pressure and the residue is distilled to give 302.9 g (83.2%) of 5,5-diethoxy-2-isopropyl-2-(2-methylphenyl-valeronitrile, b.p. 102° to 104° C. at 4 Pa.

Provenance & Evidence