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Efficient one-pot synthesis of 2-(2-hydroxyaryl)-2,4,4-trimethylchromanes from 1-(2-hydroxyaryl)ethanones

Dmitry Anatol'evich Tatarinov 1, 2
Dmitry Anatol'evich Tatarinov
, 
Elina Aleksandrovna Mikulenkova 1, 2
Elina Aleksandrovna Mikulenkova
, 
Igor Anatol'evich Litvinov 1
Igor Anatol'evich Litvinov
, 
1 A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russian Federation
2 Alexander Butlerov Institute of Chemistry, Kazan Federal University, Kazan, Russian Federation
10.1016/j.mencom.2023.10.037
Published 2023-10-18
Communication , Volume 33, Issue 6, 850-852
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Tatarinov D. A. et al. Efficient one-pot synthesis of 2-(2-hydroxyaryl)-2,4,4-trimethylchromanes from 1-(2-hydroxyaryl)ethanones // Mendeleev Communications. 2023. Vol. 33. No. 6. pp. 850-852.
GOST all authors (up to 50) Copy
Tatarinov D. A., Mikulenkova E. A., Litvinov I. A., Mironov V. F. Efficient one-pot synthesis of 2-(2-hydroxyaryl)-2,4,4-trimethylchromanes from 1-(2-hydroxyaryl)ethanones // Mendeleev Communications. 2023. Vol. 33. No. 6. pp. 850-852.
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TY - JOUR
DO - 10.1016/j.mencom.2023.10.037
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.037
TI - Efficient one-pot synthesis of 2-(2-hydroxyaryl)-2,4,4-trimethylchromanes from 1-(2-hydroxyaryl)ethanones
T2 - Mendeleev Communications
AU - Tatarinov, Dmitry Anatol'evich
AU - Mikulenkova, Elina Aleksandrovna
AU - Litvinov, Igor Anatol'evich
AU - Mironov, Vladimir Fedorovich
PY - 2023
DA - 2023/10/18
PB - Mendeleev Communications
SP - 850-852
IS - 6
VL - 33
ER -
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@article{2023_Tatarinov,
author = {Dmitry Anatol'evich Tatarinov and Elina Aleksandrovna Mikulenkova and Igor Anatol'evich Litvinov and Vladimir Fedorovich Mironov},
title = {Efficient one-pot synthesis of 2-(2-hydroxyaryl)-2,4,4-trimethylchromanes from 1-(2-hydroxyaryl)ethanones},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.037},
number = {6},
pages = {850--852},
doi = {10.1016/j.mencom.2023.10.037}
}
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Tatarinov, Dmitry Anatol'evich, et al. “Efficient one-pot synthesis of 2-(2-hydroxyaryl)-2,4,4-trimethylchromanes from 1-(2-hydroxyaryl)ethanones.” Mendeleev Communications, vol. 33, no. 6, Oct. 2023, pp. 850-852. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.037.

Keywords

[4 + 2]-cycloaddition
1-(2-hydroxyaryl)ethanones
2,4,4-trimethylchromanes
crystal structure
dehydration
Grignard synthesis

Abstract

A one-pot synthesis of 2-(2-hydroxyaryl)-2,4,4-trimethyl-chromanes in near quantitative yields is based on the reaction of 1-(2-hydroxyaryl)ethanones with methylmagnesium iodide followed by treatment with dilute sulfuric acid. The structure of 2-(2-hydroxyphenyl)-2,4,4-trimethylchromane is confirmed by X-ray diffraction.

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