NUCHLEOPHILIC SUBSTITUTION REACTION OF CYANIDE AND METHOXYDE IONS TO QUATERNARY MANNICH BASE FROM VANILLIN

https://doi.org/10.22146/ijc.21713

Bambang Purwono(1*), Estiana E.P Daruningsih(2)

(1) Organic Laboratory, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Gadjah Mada University, Sekip Utara, Jogjakarta, Indonesia 55281
(2) Organic Laboratory, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Gadjah Mada University, Sekip Utara, Jogjakarta, Indonesia 55281
(*) Corresponding Author

Abstract


The nucleophilic substitution reaction to quaternary Mannich base from vanillin has been investigated. Mannich reaction to vanillin was carried out by refluxing mixture of vanillin, formaldehyde and dimethyl amine. Quaternary ammonium halide salt was obtained from reaction of Mannich vanillin base with methyl iodide in THF solvents and yielded  93.28%. Nucleophilic substituion to the halide salts with cyanide nucleophile produced 4-hidroxy-3-methoxy-5-(cyano)methylbenzaldehyde in 54.39% yield, with methoxyde ion obtained  4-hidroxy- 3-methoxy-5-(methoxy)-methyl-benzaldehide in 67.80% yield. The nucleophilic substitution reaction showed that substituen of trimethylamino quaternary Mannich base can act as a good leaving on nucleophilic reaction substitutions.


Keywords


Mannich Reaction; Vanillin; nucleophilic substitution

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References

[1]   Sarifudin, 2002, Sintesis Antioksidan Turunan Amina dari Vanilin, Skripsi FMIPA-UGM.

[2]   Tae Kim, and Elsenbaumer, R.I., 1998, Tetrahedron Letter, 39, 1087 – 1090.

[3]   Julia, M., and  Lallemand, J.V., 1973, Bulletin De La Societe Chimique De France, 6, 2046 - 2057

[4]   Gardner, P.D., Rafsanjani, H.S. and Rand, C., 1959, J. Org. Chem., 81, 3364-3367

[5]   Yamada, K, Itoh, N., dan Iwakuma T, 1978, J.C.S.Chem.Comm, 861.



DOI: https://doi.org/10.22146/ijc.21713

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Indonesian Journal of Chemisty (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

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