Facile Synthesis of Methyl 7-Methoxy-2-naphthoate. An Improved Procedure for Monomethylation of 2,7-Naphthalenediol

Philippe Prince; Richard D. Gandour

doi:10.1055/s-1991-20743

Synlett 1991; 1991(6): 405-406
DOI: 10.1055/s-1991-20743

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Facile Synthesis of Methyl 7-Methoxy-2-naphthoate. An Improved Procedure for Monomethylation of 2,7-Naphthalenediol

Philippe Prince^* , Richard D. Gandour

^*Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803-1804, USA

Abstract

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Methyl 7-methoxy-2-naphthoate (1) is prepared in three steps from readily available 2,7-naphthalenediol (2) with an overall yield of 61%. The first step is the monomethylation of 2 by dimethyl sulfate with sodium hydroxide in a two-solvent system (CH₂Cl₂/H₂O), which represents an improvement over past methods. 7-Methoxy-2-naphthol (3) reacts with trifluoromethanesulfonic anhydride (triflic anhydride) to give the corresponding triflate. Palladium-catalyzed methoxycarbonylation of the triflate yields 1.

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