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Citation: ZHANG Cheng-Lu, NIU Ming-Ming, XU Yong-Ting, CHEN Song, SHEN Hong-Jiang, GUANG Dong, LIU Lin. Synthesis of Vanillyl Amide[J]. Chinese Journal of Applied Chemistry, ;2008, 25(6): 677-680. shu

Synthesis of Vanillyl Amide

1.
a School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
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b Analytical Center, Liaoning Normal University, Dalian 116029

Corresponding author: ZHANG Cheng-Lu,
Received Date: 4 July 2007
Available Online: 26 November 2007
Fund Project: 辽宁省科学技术研究资助项目(05L202) (05L202)

An efficient and high-yield synthesis of 3-methoxy-4-formylphenonyl p-methylbensulphonate (5) was accomplished with vanillin as the starting material in three steps.It involved the converstion of vanillin into hydrazine (4) and the metalic reduction of hydrazine 4 into the intermediate vanillic amine.The phosphonium 6 was synthesized in solid phase by the reaction of 6-bromohexyoic acid with triphenylphosphine,and then the Wittig condensation of phosphonium 6 with iso-butanol afforded 8-methoxynon-cis-6-enoic acid (7).Finally,compound 7 was connected with the amine 5,and then was hydrolyzed to the target compound under ultrasonic condition.IR,NMR and HRMS were used to confirm the structure of the title compound.
- vanillic amine,
- acylation,
- capsaicin,
- synthesis
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