The Meyers synthesis is an organic synthesis for the preparation of unsymmetrical aldehydes via hydrolysis of an oxazine. [1] [2] [3] [4] The reaction is named after the American chemist Albert Meyers.
The starting compound is a dihydro-1,3-oxazine with an alkyl group in the 2 position. The alpha proton is acidic and can be abstracted by a strong base such as butyl lithium and subsequently alkylated by an alkyl halide ( haloalkane). In the next step the nitrogen to carbon double bond ( imine) is reduced with sodium borohydride and the resulting oxazine (a hemiaminal) hydrolyzed with water and oxalic acid to the aldehyde.
References
- ^ Aldehydes from dihydro-1,3-oxazines. I. Synthesis of aliphatic aldehydes and their C-1 deuterated derivatives Albert I. Meyers, Aiko Nabeya, H. Wayne Adickes, Ieva R. Politzer J. Am. Chem. Soc. 1969; 91(3); 763-764. doi: 10.1021/ja01031a053
- ^ Aldehydes from dihydro-1,3-oxazines. II. Synthesis of .alpha.,.beta.-unsaturated aldehydes and their C-1 deuterated derivatives Albert I. Meyers, Aiko Nabeya, H. Wayne Adickes, J. Michael Fitzpatrick, G. Ray Malone, and Ieva R. Politzer pp 764 - 765; J. Am. Chem. Soc. 1969 doi: 10.1021/ja01031a054
- ^ Aldehydes from dihydro-1,3-oxazines. III. Synthesis of cycloalkanecarboxaldehydes Albert I. Meyers, H. Wayne Adickes, Ieva R. Politzer, and Warren N. Beverung pp 765 - 767; J. Am. Chem. Soc. 1969 doi: 10.1021/ja01031a055
- ^ Organic Syntheses, Coll. Vol. 6, p.905 (1988); Vol. 51, p.24 (1971). http://www.orgsynth.org/orgsyn/pdfs/CV6P0905.pdf
The Meyers synthesis is an organic synthesis for the preparation of unsymmetrical aldehydes via hydrolysis of an oxazine. [1] [2] [3] [4] The reaction is named after the American chemist Albert Meyers.
The starting compound is a dihydro-1,3-oxazine with an alkyl group in the 2 position. The alpha proton is acidic and can be abstracted by a strong base such as butyl lithium and subsequently alkylated by an alkyl halide ( haloalkane). In the next step the nitrogen to carbon double bond ( imine) is reduced with sodium borohydride and the resulting oxazine (a hemiaminal) hydrolyzed with water and oxalic acid to the aldehyde.
References
- ^ Aldehydes from dihydro-1,3-oxazines. I. Synthesis of aliphatic aldehydes and their C-1 deuterated derivatives Albert I. Meyers, Aiko Nabeya, H. Wayne Adickes, Ieva R. Politzer J. Am. Chem. Soc. 1969; 91(3); 763-764. doi: 10.1021/ja01031a053
- ^ Aldehydes from dihydro-1,3-oxazines. II. Synthesis of .alpha.,.beta.-unsaturated aldehydes and their C-1 deuterated derivatives Albert I. Meyers, Aiko Nabeya, H. Wayne Adickes, J. Michael Fitzpatrick, G. Ray Malone, and Ieva R. Politzer pp 764 - 765; J. Am. Chem. Soc. 1969 doi: 10.1021/ja01031a054
- ^ Aldehydes from dihydro-1,3-oxazines. III. Synthesis of cycloalkanecarboxaldehydes Albert I. Meyers, H. Wayne Adickes, Ieva R. Politzer, and Warren N. Beverung pp 765 - 767; J. Am. Chem. Soc. 1969 doi: 10.1021/ja01031a055
- ^ Organic Syntheses, Coll. Vol. 6, p.905 (1988); Vol. 51, p.24 (1971). http://www.orgsynth.org/orgsyn/pdfs/CV6P0905.pdf