A Tandem Aminoalkylation of Aldehydes; Application to theSynthesis of Substituted Phenols and Naphthols†

Abstract

Treatment of a protected salicylic aldehyde (2) and2-hydroxy-1-naphthaldehyde (6) with (trimethylsilyl)dialkylaminesand various nucleophiles in a 5 M diethyl ethersolution of lithium perchlorate gives a variety ofN ,N -dialkylaminophenols (4) and1-(N ,N -dialkylamino)-2-naphthols (8) in shortreaction times and in good yields.