Dimethyl Sulfoxide → 6,6-Diphenylhex-5-enoic acid

Participants

Reaction Steps

The reaction was carried out as in Example 87 using the following reagents: sodium hydride (56% dispersion in oil; 8.6 g), dimethylsulfoxide (100 mL), (4-carboxybutyl)triphenylphosphonium bromide (36.5 g), benzophenone (18.2 g), and tetrahydrofuran (100 mL). The crude product, isolated in the usual manner, was crystallized from hexane to give 16.5 g of 6,6-diphenyl-5-hexenoic acid, mp 111°-112.5° C. Anal. Calculated for C18H18O2 : C, 81.17; H, 6.81. Found: C, 81.39; H, 6.88.

Provenance & Evidence