Methanol → HCID 14986704, compound

Participants

Reaction Steps

Methanol (4136 mL) is added dropwise over about 3 hours to a mixture of 2054 g of 5-carbomethoxy-oct-7-enenitrile, 1286 g of sodium borohydride and 20.5 L of 1,2-dimethoxyethane heated at 75°. The reaction mixture is heated at 95° for 31/2 hours, stirred at room temperature overnight, and cooled to 8° C. in an ice bath. Water (21.0 L) is added slowly, the mixture is again stirred for 11/2 hours at room temperature, and then extracted with ethyl acetate (2×20 L). The combined extract is washed with brine, dried over sodium sulfate and evaporated to dryness at 65-70°/3 mm Hg. The residue is distilled to yield 6-hydroxy-5-(2-propenyl)-hexanenitrile, b.p. 113-116°/0.8 mm Hg.

Provenance & Evidence