Meyers synthesis

The Meyers synthesis is an organic chemical reaction for the preparation of aldehydes by the hydrolysis of an oxazine. The reaction is named after its discoverer, the American chemist Albert I. Meyers.

Course of the reaction

The starting compound is a dihydro-1 ,3 -oxazine with an alkyl group in the 2-position. The α - proton of the alkyl group is through the adjacent heteroatoms CH-acidic and is deprotonated by strong bases. Subsequent electrophilic alkylation with alkyl halides and reduction of the heterocycle lead to tetrahydrooxazine. Since this is a hemiaminal, formed during the hydrolysis with water and oxalic acid is a substituted aldehyde.