Benzoate → HCID 22805680, compound

Participants

Reaction Steps

After an unsuccessful attempt to convert the trimethylsilyl ether directly to the benzoate 7a (R = C6H5CO2) by heating with benzoyl chloride and lithium chloride in pyridine, the trimethylsilyl group was completely hydrolyzed by brief (about 1 minute) reflux in methanol. After removal of the methanol at reduced pressure, the benzoate-phenol mixture was treated with 2 ml of benzoyl chloride in 25 ml of pyridine for 10 minutes, followed by 2 ml of 85% lactic acid for 10 minutes to destroy excess reagent. The mixture was poured into water, extracted with ether, and the ether layer was thoroughly washed with dilute H2SO4 and saturated NaHCO3, followed by the usual work up to afford 4.02 g (theoretical yield 3.84 g) of brown crystalline solide, mp 100°-120°. An analytical sample was obtained by recrystallization from methanol, colorless plates, mp 114°-116°.

Provenance & Evidence