Benzene → 4-Dibutylamino-beta,beta-di(methylsulfonyl)styrene

Participants

Reaction Steps

A mixture of 23.3 g (0.10 mol) of 4-dibutylaminobenzaldehyde, 17 g (0.10 mol) of di(methylsulfonyl)methane, 15 mL of pyridine, 7 drops of piperidine, and 400 mL of benzene was heated at reflux for 18 hr, with continuous azeotropic separation of the water evolved. Approximately half of the benzene was removed by distillation, and 200 mL of heptane was added. Upon cooling to room temperature, a white precipitate formed. The crude product was purified by silica gel chromatography followed by micrystallization from ethanol, from toluene, and from methanol, producing 18 g (46%) of (2). A sample of (2) that was sublimed in vacuo melted at 114.5°-115° C.

Provenance & Evidence