4-Methylbenzaldehyde → (+/-)-3,3-Dimethyl-1-p-tolyl-butan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-methylbenzaldehyde (1.51 g, 12.6 mmol) in THF (30 mL) at 0° C., add neopentyl magnesium chloride (33.0 mL, 16.34 mmol, 0.5-1M in ether) and continue stirring at 0° C. for 1 h. Dilute with saturated aqueous NH4Cl, extract three times with EtOAc, dry over anhydrous Na2SO4, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (95:5) to give the desired intermediate as a colorless oil (2.15 g, 89%).

Provenance & Evidence