Birch Reductive Alkylation of Methyl<i>m</i>-(Hydroxymethyl)benzoate Derivatives and the Behavior of<i>o</i>- and<i>p</i>-(Hydroxymethyl)benzoates under Reductive Alkylation Conditions

Abstract

Birch reductive alkylation of methyl m-(hydroxymethyl)benzoate derivatives, using lithium in ammonia-tetrahydrofuran in the presence of tert-butyl alcohol, can be achieved without significant loss of benzylic oxygen substituents. Similar treatment of o- and p-(hydroxymethyl)benzoate derivatives results largely in loss of benzylic oxygen substituents. The results are rationalized by computations describing electron density patterns in the putative radical anion intermediate involved in these reactions.