2-Chloroethanol → (2-Decyloxy)ethanol

Participants

Reaction Steps

44.88 g (800 mmol) of fine powdered potassium hydroxide is added to 32.93 g (200 mmol) of the tetrahydropyranyl ether of 2-chloroethanol, 1 g (3.6 mmol) of tetrabutylammonium chloride and 20 g (126.36 mmol) of decan-1-ol in 300 ml of toluene, and it is refluxed for 24 hours. Solid is filtered out, and the filtrate is evaporated to the dry state. 500 ml of ethanol/50 ml of 10% aqueous hydrochloric acid are added to the residue (oil) that is thus obtained, and it is stirred for one hour at room temperature. It is evaporated to the dry state in a vacuum, and the residue is chromatographed on silica gel (mobile solvent: hexane/acetone=20:1).

Provenance & Evidence