Water → 3,3-Dimethylhex-5-enyl 4-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

In a 500-mL, two-necked round-bottom flask, 3,3-dimethylhex-5-en-1-ol (5.30 g, 0.041 mol) and triethylamine (16 mL, 0.057 mol) were dissolved in dichloromethane (110 mL), and then the mixture was cooled, under nitrogen atmosphere, in an ice bath to 5° C. A dichloromethane (10 mL) solution of 4-nitrobenzoyl chloride (9.1 g, 0.049 mol) was added dropwise in 20 minutes. After the mixture had been stirred at 5-10° C. for 1 hour, water was added. The organic layer was washed with acid, water, brine, dried over sodium sulfate, and filtered. After evaporation of the solvent, the crude product was purified by column chromatography (silica gel; ethyl acetate/hexanes 1/9 as eluant) to give the title compound as a yellow liquid.

Provenance & Evidence