Sulfuric Acid → Oleyl Alcohol

Participants

Reaction Steps

A solution of compound II (12 g) in 50 ml of dry ether was slowly dripped into a stirred suspension of 2 g of lithium aluminum hydride in 100 ml of dry ether. Gentle refluxing was maintained during addition, and the mixture was then refluxed for an additional 30 minutes. The mixture was chilled in an ice bath and treated gradually with 35 ml of ice water followed by 50 ml of cold 10% H2SO4. The ether layer was separated, the aqueous layer was shaken with two portions of ether, and the combined ether layers were dried over anhydrous Na2SO4. Evaporation of the solvent and distillation of the residue gave 11.1 g (97%) of compound III which boiled at 150° (0.02 mm), nD25 1.4608.

Provenance & Evidence