3,4-Dimethylaniline → 2-(3,4-Xylyl)thiophene
反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])N.[S:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.N(OCCCC)=O>>[C:4]1([C:11]2[S:10][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]([CH3:9])=[C:2]([CH3:1])[CH:3]=1参加物
4
実験手順
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.