Sciencemadness Discussion Board

synthesis of 4-fluorophenyl-2-nitropropene with methylammonium acetate catalyst

stoichiometric_steve - 23-1-2006 at 09:54

1 eq. 4-fluorobenzaldehyde was gently refluxed with 10 mol% eq. of methylammonium acetate, 1.2 eq. of nitroethane and 20 wt.% IPA as solvent for 8 hours, obtaining an amber solution, which upon cooling yields very pure crystal platelets of 4-fluorophenyl-2-nitropropene (88%), 110g out of 100g 4-fluorobenzaldehyde. the latter can be used without further purification because the catalyst is just so clean and produces hardly any polymer in contrast to the dirty n-butylamine.

yields with plain benzaldehyde (6hrs reflux in IPA): 85%
yield with piperonal (1.5hrs reflux in IPA): 72%

[Edited on 23-1-2006 by stoichiometric_steve]