Method for conducting organic reactions using guanidinium salt as phase transfer catalyst
AssigneeGeneral Electric Company
InventorsDaniel J. Brunelle, Deborah A. Haitko, James P. Barren, Sunita Singh
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Abstract
Reactions between a solid polar and a non-polar compound, especially nucleophilic aromatic substitution reactions between an alkali metal salt of a hydroxyaromatic compound or thio analog thereof and an activated halo- or nitro-substituted aromatic compound, are conducted in a non-polar organic solvent such as toluene or xylene, in the presence of a hexaalkylguanidinium or .alpha.,.omega.-bis(pentaalkylguanidinium)alkane salt, or a corresponding heterocyclic salt, as a phase transfer catalyst. The method is particularly useful for the preparation of bisimides from bisphenol A or 4,4'-biphenol salts and 4-nitro- or 4-halophthalimides.
Claims21
A method for effecting reaction in a non-polar organic solvent between an alkali metal salt of a hydroxyaromatic compound or thio analog thereof and a substituted imide having the formula
- wherein A is an aromatic radical, R.sup.4 is hydrogen or a hydrocarbon radical containing about 1-13 carbon atoms and X.sup.2 is halo or nitro, which comprises conducting said reaction in the presence of at least one guanidinium or a, .omega.-bis(guanidinium)alkane salt of the formula ##STR4## as a phase transfer catalyst, wherein each of R.sup.5, R.sup.6, R.sup.7 and R.sup.8 is a primary alkyl radical or at least one of the R.sup.5 -R.sup.6 and R.sup.7 -R.sup.8 combinations with the connecting nitrogen atom forms a piperidino, pyrrolo or morpholino radical, R.sup.9 is a primary alkyl radical, R.sup.10 is a bis(primary alkylene) radical, X is an anion and n is 1 or 2.
Dependencies are inferred from the claim text.