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Concurrent synthesis of vanillin and isovanillin

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Abstract

A method for concurrent synthesis of vanillin and isovanillin has been developed by a nonregioselective Vilsmeier–Haack reaction of O-alkyl guaiacols. O-Alkylation of guaiacol provided the corresponding O-alkyl guaiacol (1), which was then formylated with N-methylformanilide/phosphorus oxychloride to give a mixture of 4-alkoxy-3-methoxy-benzaldehyde (2) and 3-alkoxy-4-methoxybenzaldehyde (3). Finally, the obtained mixture underwent a selective dealkylation by anhydrous aluminium trichloride, while leaving methyl groups intact to simultaneously achieve the significant fine chemicals vanillin and isovanillin.

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Acknowledgment

We thank the National Natural Science Foundation of China (Project No. 21176074) for financial support.

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Authors and Affiliations

  1. School of Pharmacy, East China University of Science and Technology, Campus P.O. Box 363, 130 Meilong Road, Shanghai, 200237, China

    Wei-Bin Huang, Cai-Yan Du, Jian-An Jiang & Ya-Fei Ji

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  1. Wei-Bin Huang
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  2. Cai-Yan Du
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  3. Jian-An Jiang
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  4. Ya-Fei Ji
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Correspondence to Ya-Fei Ji.

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Huang, WB., Du, CY., Jiang, JA. et al. Concurrent synthesis of vanillin and isovanillin. Res Chem Intermed 39, 2849–2856 (2013). https://doi.org/10.1007/s11164-012-0804-6

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