Dimethyl Sulfoxide → 8,8-Diphenyl-7-octenoic acid

Participants

Reaction Steps

The reaction was carried out as in Example 87 using the following reagents: sodium hydride (56% dispersion in oil; 8.36 g); dimethylsulfoxide (100 mL), (6-carboxyhexyl)triphenylphosphonium bromide (37.7 g), benzophenone (17.5 g); and tetrahydrofuran (100 mL). The crude product, isolated in the usual way, was recrystallized from hexane (200 mL) to yield 16.6 g of 8,8-diphenyl-7-octenoic acid, mp 88°-89° C. Anal. Calculated for C20H22O2 : C, 81.60; H, 7.53. Found: C, 81.34; H, 7.25.

Provenance & Evidence