Acetic Anhydride → 7-Octenenitrile

Participants

Reaction Conditions

Reaction Steps

Into a nitrogen-substituted 500 mL volume flask, toluene (200 g) and the crude 7-octenal (30.5 g) (90.0% in gas chromatography simple area %, net: 27.5 g, 0.22 mol; cis-6-octenal: 6.3% in gas chromatography simple area %, tras-6-octenal: 4.0% in gas chromatography simple area %) obtained by the technique of Synthesis Example 1 were charged. An aqueous solution of 35.5% by mass hydroxylamine sulfate (55.5 g; net: 19.7 g, 0.12 mol) was added thereto, and then the mixture was cooled to 0° C. An aqueous solution of 18% by mass sodium hydroxide (53.3 g; net: 9.6 g, 0.24 mol) was added thereto at a temperature in a range of 10 to 20° C. over 1.0 hour. After completion of the reaction, water (100 g) was added and the resulting two layers were separated. After acetic anhydride (24.5 g, 0.24 mol) was added to the organic layer, azeotropic dehydration was carried out by heating at an internal temperature of 120° C. for 3 hours. The organic layer was separated, and the obtained organic layer was distilled under a reduced pressure of 670 Pa, to obtain crude 7-octenonitrile (25.0 g) (90.2% in gas chromatography simple area %, 22.5 g, 0.18 mol; cis-6-octenonitrile: 3.9% in gas chromatography simple area %, tras-6-octenonitrile: 3.4% in gas chromatography simple area %) as a distillate.

Provenance & Evidence