Journal of Organic Chemistry p. 3022 - 3026 (1983)
Update date:2022-08-11
Topics:
Paradisi, Cristina
Quintily, Ugo
Scorrano, Gianfranco
Reactions of 1-chloro-4-nitrobenzene (1) with alkoxide ions in the parent alcohols do not afford satisfactory yields of the expected alkyl 4-nitroaryl ether except in the case of the short-chain primary alcohols.We report that in the model reaction of 1 with KOH in 2-propanol good yields of 1-isopropoxy-4-nitrobenzene (2) are obtained provided Bu4NBr or alkali ion complexing agents such as 18-crown-6, Carbowax 20M, MPEG 5000, and Triton X-100 are present.Low molecular weight ethers, like glyme-5, are less effective, with ethylene glycol dimethyl ether having no effect at all.Work at temperatures below the solution boiling point is recommended to avoid competitive reduction of the NO2 group.The preparative value of Bu4NBr additions in analogous reactions of 1 to give 4-O2NC6H4OR ethers (3) is also very significant when R is primary, secondary, and aryl (1-octyl, sec-butyl, phenyl).The reaction fails when R = tert-butyl and 4-O2NC6H4.
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