Two efficient syntheses of 5-methoxy-and 8-methoxy-3-methyl-2-tetralone and the synthesis of the 7-methoxy isomer via a different route are described. Also reported is the synthesis of 8-methoxy-3, 3-dimethyl-2-tetralone. The regioselectivity of lithium carbanion formation in 1, 6-, 1, 7-, and 2, 7-dihydroxynaphthalene is discussed. The latter compound undergoes dimetalation more easily than the other isomers.