3,4-Dimethylaniline → 2-(3,4-Xylyl)thiophene

Participants

Reaction Steps

A solution of 182 g (1.50 moles) of 3,4-dimethylaniline, m.p. 49°-51° C. in 3000 ml (38 moles) of thiophene was treated with 226 ml (2.00 moles) of n-butyl nitrite. The solution was allowed to stand at room temperature for one week. Unreacted thiophene was removed by distillation with a steam bath. The residue was distilled at reduced pressure to give 75 g (27%) of 2-(3,4-xylyl)thiophene, b.p. 107°-122° (0.08 mm). Vapor phase chromatography showed the presence of about 2% of the xylidine starting material, removed by washing first with two 100-ml portions of 10% hydrochloric acid followed by two 150-ml portions of distilled water.

Provenance & Evidence