4-Methylbenzyl alcohol → HCID 57845343, compound

Participants

Reaction Conditions

Reaction Steps

4-Methylbenzyl alcohol (37.6 g, 308 mmol) was added to a solution of 1,1′-carbonyldiimidazole (50.0 g, 308 mmol) in DMF at RT and stirred for 1 h. 4-Piperidone hydrate hydrochloride (commercially available from Sigma-Aldrich, 47.0 g, 308 mmol) was added, resulting in a reaction mixture that was then heated to 50° C. and stirred for 15 h. The reaction mixture was diluted with EtOAc and washed with 0.1 M HCl, H2O (four times), and brine, dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (step gradient elution: 10%, 25%, 50% EtOAc in hexanes) produced the title compound (42.4 g, 85% yield) as a clear oil.

Provenance & Evidence