Process for synthesizing benzoic acids

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic halides

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C07C 5158

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active

061245003

ABSTRACT:
A nucleophilic substitution reaction on optionally substituted dihalobenzenes is carried out in the presence of an optional catalyst followed by formation of and subsequent carboxylation of a Grignard reaction intermediate. In particular the present invention provides a process leading to optionally substituted hydroxybenzoic, alkanoyloxybenzoic, formyloxybenzoic and alkoxybenzoic acids from 1-substituted 2,6-dihalobenzenes. The invention also provides a process for the direct formation of an acyl chloride from a Grignard reagent by quenching with phosgene.

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S. Sandler & W. Karo "Organic Functional Group Preparations." Academic Press: 1968.
M.S. Carpenter, et al., J. Org. Chem., vol. 20 (4), pp. 401-411 (1955).
T.M. Cresp, et al., J. C. S. Perkin I, pp. 2435-2447 (1974).
Nucleophilic Aromatic Substitution Reactions of Unactivated Aryl Chlorides with Methoxide Ion in Hexamethylphosphoramide, James E. Shaw, et al., J. Org. Chem., vol. 41 (4), pp. 732-733 (1976).
Reaction ID 827509, Beilstein Institut fur Literatur der organischen Chemie (1988-1998) and Justus Liebigs Ann. Chem., vol. 148, p. 222 (1868).

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