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Citation: Liu Qichao, Zhou Hongyong, Wang Jiaxi. Oxa-Michael Addition of Acrylamide: Synthesis of β-Alkoxypropionamide[J]. Chemistry, ;2018, 81(7): 604-609. shu

Oxa-Michael Addition of Acrylamide: Synthesis of β-Alkoxypropionamide

School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130

Corresponding author: Wang Jiaxi, wangjiaxi@hebut.edu.cn
Received Date: 12 April 2018
Accepted Date: 2 May 2018

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A series of β-alkoxypropionamides were synthesized by the oxa-Michael addition reaction of alcohol with acrylamide. The structure of product was characterized by NMR and HRMS. The effects of catalyst, reaction temperature, and ratio of reactants on the reaction were explored. At 40℃, the oxa-Michael addition reaction of primary alcohol with acrylamide went smoothly under promotion of 5 (mol)% activated potassium carbonate. The activity of secondary alcohol is lower. As for tertiary alcohol and phenol, almost no reaction was observed. At higher temperature, the acrylamide underwent the aza-Michael addition to generate dimer of acrylamide. The reaction of alcohol with acrylamide can be run at equivalent ratio as the solvent-free mode. Intramolecular hydrogen bond can increase the reactivity of secondary hydroxyl group.
- Oxa-Michael addition,
- Alcohol,
- Glycerol,
- Acrylamide
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