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ChemicalBook CAS DataBase List 1,4-Diacetylbenzene

1,4-Diacetylbenzene synthesis

13synthesis methods
-

Yield:1009-61-6 92%

Reaction Conditions:

with pyridine;N-hydroxyphthalimide;tetrabutylammonium tetrafluoroborate;oxygen in 2,2,2-trifluoroethanol;acetonitrile at 35;Electrolysis;

Steps:

2.2.1 Procedure for mono-oxidation

General procedure: An undivided cell was equipped with a magnet stirrer, platinum plate electrode (1.0×1.0×0.3 cm3), as the working electrode and counter electrode. Substrate (0.5 mmol),nBu4NBF4 (0.5 mmol, 164.6 mg), N-hydroxyphthalimide (NHPI, 0.1 mmol, 16.3 mg), and pyridine (1.0 mmol, 82 μL)were added to MeCN/2,2,2-trifluoroethan-1-ol (TFE) (5:1,3 mL). The electrolysis was conducted in an undivided cell equipped with O2 balloon at a constant current of 5 mA at room temperature (25-30 °C). When the reaction was completed, the solvent was removed under reduced pressure and the remaining crude product was purified by column chromatography over silica gel (petroleum ether/ethyl acetate(PE/EA)=30:1-10:1) to afford the corresponding aromatic ketone product.

References:

Li, Zhibin;Zhang, Yan;Li, Kuiliang;Zhou, Zhenghong;Zha, Zhenggen;Wang, Zhiyong [Science China Chemistry,2021,vol. 64,# 12,p. 2134 - 2141]

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