Method for making aromatic ethers using diorganoamino pyridinum

Details Method for making aromatic ethers using diorganoamino pyridinum Method for making aromatic ethers using diorganoamino pyridinum

1983-04-28

1985-04-23

Jiles, Henry R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548480, 548455, 546304, 260465F, 568 31, 568 37, 568 43, 568 45, 568315, 568584, C07B 2900, C07D207444, C07C 4101

Patent

active

045131414

ABSTRACT:
A method is provided for making aromatic ethers by effecting the displacement of reactive radicals on an activated aromatic nucleus such as a phthalimide with a mono or bisalkali metal phenoxide in the presence of an organic solvent and a dialkylamino branched alkyl substituted pyridinium salt as a phase transfer catalyst. Improved yields of bis(aromatic ethers) are achieved without the production of undesirable by-products, such as alkylated phenols.

REFERENCES:
patent: 3852242 (1974-12-01), White
patent: 4140853 (1979-02-01), Vorbrueggen
patent: 4158093 (1979-06-01), Bailey et al.
patent: 4202993 (1980-05-01), Takekoshi
patent: 4257953 (1981-03-01), Williams et al.
patent: 4273712 (1981-06-01), Williams
Merck Index, 9th Edition entry #1987 (1976).
4-Dialkylaminopyridines as Highly Active Acylation Catalysts, Hofle et al., Angew. Chem. Int. Ed. Engl. 17, 569-583 (1978).
Phosphoramides; VIII.sup.1. Phosphorus Pentoxide/Amine Mixtures as Reagents in a Facile Synthesis of Dialkylaminopyridines, Pedersen et al., Synthesis, 844, (1978).
Synthesis and Catalytic Activity of Polymer-Bound 4-(N-Benzyl-N-Methylamino)Pyridine, Tomoi et al., Makromol, Chem., Rapid Commun. 3, 537-542 (1982).
Phase Transfer Catalysis, Starks et al., Academic Press, New York (1978).
Phase Transfer Catalysis, Dehmlow et al., Verlag Chemie, Stuttgart, Germany (1980).
Phase Transfer Catalysis in Organic Synthesis, Weber et al., Springer-Verlag, New York (1977).

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