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

https://doi.org/10.22146/ijc.21789

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

(1) Organic Chemistry Laboratory, Chemistry Department, Faculty of Mathematics and Natural Sciences University of Gadjah Mada, Sekip Utara, Yogyakarta 55281
(2) Organic Chemistry Laboratory, Chemistry Department, Faculty of Mathematics and Natural Sciences University of Gadjah Mada, Sekip Utara, Yogyakarta 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. Reaction with methoxyde ion yielded 4-hydroxy- 3-methoxy-5-(methoxy) -methylbenzaldehyde in 67.80% yield. The nucleophilic substitution reaction showed that trimethylamino substituent of quaternary Mannich base can act as a good leaving group on nucleophilic substitution reactions.


Keywords


Mannich reaction; vanillin; nucleophilic substitution

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References

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

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

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

[4] Szmuszkovics, J., 1960, J. Chem. Soc., 82, 1180-1186.



DOI: https://doi.org/10.22146/ijc.21789

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

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