Acetone Cyanohydrin → 2-(7-Hydroxyheptyl)-3-oxocyclopentanecarbonitrile

Participants

Reaction Steps

A mixture of 2-(7-hydroxyheptyl)-2-cyclopenten-1-one (17 g., 0.087 mole), acetone cyanohydrin (8.5 g., 0.1 mole), 6% aqueous sodium carbonate (8 ml.) and methanol (50 ml.) was stirred and heated under reflux for 4 hours. Methanol was removed in vacuo, water (100 ml.) was added and the mixture was extracted with diethyl ether and dried over magnesium sulphate. The solvent was removed by evaporation, and the residue was distilled under reduced pressure to give 2-(7-hydroxyheptyl)-3-oxocyclopentanecarbonitrile (13.3 g., 68%), b.p. 144°-182°C./0.15 mm.Hg, nD25 1.4795.

Provenance & Evidence