Dimethyl Sulfoxide → 7,7-Diphenylhept-6-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), (5-carboxypentyl)triphenylphosphonium bromide (37.64 g); benzophenone (18 g) and tetrahydrofuran (100 mL). The acid, isolated in the normal manner, was crystallized from hexane to give 16.3 g of 7,7-diphenyl-6-heptenoic acid, mp 71.5°-72.5° C. A portion was recrystallized from hexane to give the analytical sample, mp 72.5°-73.5° C. Anal. Calculated for C19H20O2 : C, 81.40; H, 7.19. Found: C, 81.61; H, 7.40.

Provenance & Evidence