3-Allyl Salicylaldehyde is a synthetic intermediate for the sythesis of 3-aminoflavones. Flavonoids have been studied for their antiproliferative activity and in vitro cytotoxicity. Used in the prepar
ation of oxazole derivatives. Used in the preparation of imidazole scaffold-based 2-substituted benzofurans for application against human tumor cell lines. Also a reagent in the synthesis of antioxida
nt and antimicrobial novel chalcones.
3-Allylsalicylaldehyde is a synthetic intermediate for the synthesis of 3-aminoflavones. Flavonoids have been studied for their antiproliferative activity and in vitro cytotoxicity. It is used in the preparation of oxazole derivatives and also imidazole scaffold-based 2-substituted benzofurans for application against human tumor cell lines. It is a reagent in the synthesis of antioxidant and antimicrobial novel chalcones.
The general procedure for the synthesis of 3-allyl-2-hydroxybenzaldehyde from formaldehyde and 2-allylphenol was as follows: 13.5 g (0.1 mol) of 2-allylphenol and 100 mL of acetonitrile were added to a three-necked flask, and 6.5 g of paraformaldehyde, 22 g (0.39 mol) of anhydrous magnesium chloride, and 0.02 mol of triethylamine were added sequentially under stirring conditions. The reaction mixture was refluxed for 4 h. The reaction solution was poured into ice water and the pH was adjusted with aqueous hydrochloric acid to 5. It was extracted twice with ethyl acetate, the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, 11 g of solid product was obtained in 68% yield. Mass spectrometry analysis showed a molecular ion peak of 163 (M + 1).
[1] Patent: US2012/142921, 2012, A1. Location in patent: Page/Page column 13
[2] Patent: EP2468730, 2012, A1. Location in patent: Page/Page column 14
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