Method for producing 2-chloromethylphenyl acetic acid...

Details Method for producing 2-chloromethylphenyl acetic acid... Method for producing 2-chloromethylphenyl acetic acid...

2003-02-06

2009-02-10

Oh, Taylor Victor (Department: 1625)

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

Organic compounds

Carboxylic acid esters

C564S147000

Reexamination Certificate

active

07488840

ABSTRACT:
The invention relates to a method for producing 2-chloromethylphenyl acetic acid derivatives of formula (I), in which X represents C1-C4alkoxy or methylamino, by cleaving the ether bonds in compounds of formula (II), in which R represents C1-C4alkyl, C1-C4alkoxy, C1-C2alkyl halide, C1-C4alkylcarbonyl, C1-C4alkylcarbonyloxy, halogen, nitro or cyano, and X has the above-mentioned meaning. The inventive method is characterized in that the transformation takes place in the presence of hydrogen chloride and of an inert solvent, and in that a catalyst selected from the group comprised of: iron, indium or halogenides, oxides or triflates thereof is added to the reaction mixture.

REFERENCES:
patent: 6114342 (2000-09-01), Oberdorf et al.
patent: WO 97 21686 (1997-06-01), None
Moody et al, Indium As a Reducing Agent: Deprotection of 4-Nitrobenzyl Ethers and Esters, Synlett 1999, No. 10, p. 1575-1576.
Jempty et al., “Iron trichloride/silicon dioxide reacts as oxidant or Lewis aci with phenol ethers”, Journal of Organic Chemistry (1981) 46(22), 4545-51.
Frost et al., “Indium triflate: An Efficient Catalyst for the Friedel-Crafts Acylation of Aromatics”, Fourth International Electronic Conference on Synthetic Organic Chemistry, Sep. 1-30, 2000.
Vankar et al., “Selective Cleavage of Benzyl Ethers using the Boron Trifluoride-Ether and Sodium Iodide Reagent Systems”, J. Chem. Research (S), 1985, 232-233.

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