2,7-Dimethoxynaphthalene → 7-Methoxy-2-tetralone

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Reaction Steps

2,7-dimethoxynaphthalene of formula XXV, ##STR36## is subjected to the action of sodium metal, in the heated state and in the presence of an anhydrous alcohol, to form 7-methoxy-1,2,3,4-tetrahydro-2-naphthalenone of formula XXVI, ##STR37## which is then reacted in the heated state in an alcoholic solvent with a hydroxylamine salt to form 7-methoxy-1,2,-3,4-tetrahydro-2-naphthalenone oxime of formula XXVII, ##STR38## which is then subjected to a catalytic hydrogenation, in solution in an alcohol, in the presence of Raney nickel and ammonia, to form 2-amino-7-methoxy-1,2,3,4-tetrahydronaphthalene of formula XXVIII, ##STR39## which is condensed with acetic anhydride in acetic acid medium to form 2-acetamido-7-methoxy-1,2,3,4-tetrahydronaphthalene of formula XXIX, ##STR40## which is subjected to the action of boron tribromide, at room temperature in a halogenated organic solvent, to form 2-acetamido-7-hydroxy-1,2,3,4-tetrahydronaphthalene of formula XXX, ##STR41## which is then reacted with chloroacetonitrile, in the presence of boron trichloride and aluminum chloride, to form 2-acetamido-6-(2-chloro-1-oxoethyl)-7-hydroxy-1,2,3,4-tetrahydronaphthalene of formula XXXI, ##STR42## which is subjected to the action of triethylamine, in the heated state in a halogenated organic solvent, to form 7-acetamido-2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan-3-one of formula XXXII, ##STR43## which is then either

Provenance & Evidence