ESTONIAN ACADEMY
PUBLISHERS
eesti teaduste
akadeemia kirjastus
PUBLISHED
SINCE 1952
 
Proceeding cover
proceedings
of the estonian academy of sciences
ISSN 1736-7530 (Electronic)
ISSN 1736-6046 (Print)
Impact Factor (2022): 0.9
Short communication
Uncommon reaction in 4-formyl phenols – substitution of the formyl group; pp. 1–5
PDF | https://doi.org/10.3176/proc.2024.1.01

Authors
Eleana Lopušanskaja, Anne Paju, Margus Lopp
Abstract

4-formyl phenols with electron donating groups in ortho-position react with active alkyl halides in three directions: Williamson reaction up to 48%, aromatic substitution of the formyl group up to 36%, and addition to the ortho-position with dearomatization of the ring up to 10%. The ratio of the products depends on the substituents in the benzene ring and the used alkali and additives.

References

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https://doi.org/10.1002/jlac.19134010103

2. Tarbell, D. S. The Claisen rearrangement. In Organic ReactionsII. John Wiley & Sons, New York, 1944, 1–48. 

3. Damodar, K., Kim, J.-K. and Jun, J.-G. Synthesis and pharmacological properties of naturally occurring prenylated and pyranochalcones as potent anti-inflammatory agents. Chin. Chem. Lett., 2016, 27, 698–702. 
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4. Lopušanskaja, E., Kooli, A., Paju, A., Järving, I. and Lopp, M. Towards orto-selective electrophilic substitution/addition to phenolates in anhydrous solvents. Tetrahedron, 2021, 83, 131935. 
https://doi.org/10.1016/j.tet.2021.131935

5. Kooli, A., Shalima T., Lopušanskaja E., Paju A. and Lopp M. Selective C-alkylation of substituted naphthols under non-aqueous conditions. Tetrahedron, 2021, 95, 132278. 
https://doi.org/10.1016/j.tet.2021.132278

6. Lopušanskaja, E., Paju, A., Järving, I. and Lopp, M. A direct alkylation of resorcinols. Synth. Commun., 2023, 53, 1216– 1226. 
https://doi.org/10.1080/00397911.2023.2214645

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