- Regioselective Monomethylation of Unsymmetrical Naphthalenediols with Methanolic HCl
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Treatment of naphthalene-1,3-diol and naphthalene-1,7-diol with methanol containing dry hydrogen chloride at room temperature gives exclusively 3-methoxy-1-naphthol and 7-methoxy-1-naphthol, respectively.Of the other two unsymmetrical naphthalenediols, the 1,2-isomer was unreactive and the 1,6-isomer gave a mixture of regioisomers under the same conditions.Two symmetrical diols (the 1,5- and 2,7-isomers) examined by the same procedure gave the monomethyl ethers in 60-70percent yields.
- Bell, Kevin H.,McCaffery, Leslie F.
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p. 731 - 737
(2007/10/02)
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- HALOGENATION REGIOSELECTIVE EN SERIE AROMATIQUE-II CHLORATION DES NAPHTOLS ET LEURS ETHERS A L'AIDE DE REACTIFS METTANT EN JEU DES INTERACTIONS DU TYPE DONNEUR-ACCEPTEUR
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The regispecific chlorination of naphtols by hexachlorocyclohexadienones as selective chlorinating reagents is described.The selectivity attained is better than that which we have obtained with phenol derivatives and confirms the importance of the donor-acceptor interaction between the reagent and the naphthol during the chlorination.
- Guy, Alain,Lemaire, Marc,Guette, Jean-Paul
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p. 2347 - 2354
(2007/10/02)
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