Methanol → HCID 14986704, compound

Participants

Reaction Steps

Methanol (4136 ml) is added dropwise over about 3 h to a mixture of 2054 g of 5-methoxycarbonyl-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 3.5 h, stirred at room temperature overnight, and cooled to 8° in an ice bath. Water (21.0 l) is added slowly, the mixture is again stirred for 1.5 h 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 (=4.00 mbar). The residue is distilled to yield 6-hydroxy-5-(2-propenyl)-hexanenitrile, b.p. 113°-116°/0.8 mm Hg (=1.07 mbar).

Provenance & Evidence