Journal
RESEARCH ON CHEMICAL INTERMEDIATES
Volume 39, Issue 6, Pages 2849-2856Publisher
SPRINGER
DOI: 10.1007/s11164-012-0804-6
Keywords
Concurrent synthesis; Vanillin; Isovanillin; Vilsmeier-Haack reaction; Selective dealkylation
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Funding
- National Natural Science Foundation of China [21176074]
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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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