α-Eucaine

α-Eucaine (alpha-eucaine) is a drug that was previously used as a local anesthetic.

[1] It was designed as an analog of cocaine and was one of the first synthetic chemical compounds to find general use as an anesthetic.

[2] The Aldol condensation between two equivalents of acetone gives Mesityl oxide [141-79-7] (1) (isophorone is a side-product of this reaction).

Esterification of the tertiary alcohol with benzoyl chloride gives (6).

Pinner reaction of the nitrile with EtOH/H+ affords alpha-eucaine (7).

Background: [ 3 ]