Benzyl Alcohol → Benzyl 8-bromooctanoate

Participants

Reaction Steps

There were dissolved 11.6 g (52 mmol) of 8-bromooctanoic acid in 100 ml of CCl4 and around 5° C. (ice bath), there were added to the solution 5.41 g (50 mmol) of benzyl alcohol and 2.5 mmol of 4-pyrrolidino-pyridine catalyst. Thereafter, a solution of 10.73 g (52 mmol) of dicyclohexylcarbodiimide (DCC) in 10 ml of carbon tetrachloride was added portion-wise under stirring. The precipitation of the expected dicyclohexylurea (DCU) was effective after a few min and the temperature was allowed to come back to room temperature. After ½ hr, the reaction was complete as checked by TLC (hexane/ether 1:1). Then after about 1 hr, 0.5 ml of AcOH were added to quench remaining DCC and the DCU was filtered out after about one hour (yield 11.2 g=100%).

Provenance & Evidence