Dimethylformamide → 5-Carbomethoxy-oct-7-enenitrile

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Reaction Steps

Thionyl chloride (1.125 L, 1.835 kg, 15.42 mol) is cooled to 0° C., and dimethylformamide (1.199 L, 1.132 kg, 15.50 mol) is added dropwise over a period of 2 hours keeping the temperature below 10° C. After the addition is complete the reaction is allowed to come to room temperature over 2 hours. To this is then added 5-carbomethoxy-oct-7-enoic acid amide (see example 22c, 2.671 kg, 13.42 mol) neat over a period of 3 hours. The reaction is allowed to stir at room temperature for 18 hours and is combined with material from a similar run and then diluted with ethyl ether (35 L). The solution is cooled to 0° C. and is admixed with 8 kg of ice and 12 L of water. The mixture is stirred for 30 minutes and is then basified with ammonium hydroxide (12 L, 2.5 M). The layers are separated and the organic phase is washed with water (12 L) and brine (12 L) and dried over anhydrous sodium sulfate (7.5 kg). This is then filtered and evaporated to yield a crude oil which is redissolved in ethyl ether (24 L) and this solution is stirred over 7 kg of silica gel for several hours. After filtration and evaporation there is obtained partially purified material which is then distilled to obtain 5-carbomethoxy-oct-7-enenitrile, b.p. 118-120° /0.15 mm Hg.

Provenance & Evidence