tert-Butanol → 9-tert-Butoxynonan-1-ol

Participants

Reaction Steps

200 g (2.7 mol) of tert-butanol, 100 g (0.625 mol) of 1,9-nonanediol and 2 g of sulfuric aid were placed in a 500 ml round bottomed flask, and refluxed with heat for 5 hours, followed by neutralizing with an aqueous sodium hydroxide solution. After unreacted tert-butanol was evaporated, hexane was added and stirred. The diol insoluble in hexane was discarded by filtration. The hexane layer was washed with water, and dried with anhydrous sodium sulfate. After filtration, the solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/chloroform) to obtain 35 g of 9-tert-butoxy-1-nonanol as a colorless oil.

Provenance & Evidence