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Synthesis 1987; 1987(10): 922-924
DOI: 10.1055/s-1987-28124
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Control of the Birch Reduction of m-Anisic Acid to Produce Specific 3-Oxocyclohexenecarboxylic Acids

Francis X. Webster* , Robert M. Silverstein
  • *State University of New York, College of Environmental Science and Forestry, Syracuse, NY 13210, U.S.A.
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Publication Date:
12 September 2002 (online)

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An efficient method is reported of synthesizing relatively large quantities of methyl 3-oxo-1-cyclohexenecarboxylate (2b), a useful dienophile and photoreagent, from m-anisic acid (3) through the Birch reduction. Treating 3 with lithium in liquid ammonia produces any one of the four specific 3-oxocyclohexene carboxylic acids depending on the conditions selected.