ChemicalBook CAS DataBase List Acetophenone

Acetophenone synthesis

15synthesis methods

Product Name:Acetophenone
CAS Number:98-86-2
Molecular formula:C8H8O
Molecular Weight:120.15

From benzene and acetylchloride in the presence of aluminum chloride or by catalytic oxidation of ethyl benzene; also prepared by fractional distillation and crystallization from the essential oil of Stirlingia latifolia.

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Yield:98-86-2 100%

Reaction Conditions:

with water;sodium hydroxide at 20; for 0.0833333 h;Microwave irradiation;

Steps:

general procedure for the oxidation of benzyl halides with 4-hydroxypyridinium nitrate SiO₂under microwave irradiation

General procedure: A mixture of benzyl halide (10 mmol) and H₂O (20 ml) was stirred, and then the mixture was added to 4-hydroxypyridinium nitrate functionalized silica gel (2.46 g,11 mmol) and stirred. The reaction was done at ambient temperature for half the time indicated in Table 2 by microwave and then sodium hydroxide solution (0.440 g,11 mmol, in 10 ml H2O) was added dropwise over a period of 5 min at room temperature with vigorous stirring. The mixture was irradiated again for the other half time indicated in Table 2. The progress of the reaction was monitored by TLC (silica gel,n-hexane: pet. ether (1:3) as eluent). When the reaction was complete, the reaction mixture was cooled and extracted with diethyl ether (320 ml), washed with cold water, and dried over anhydrous sodium sulfate After filtration, the removal of solvent gave a crude product which was passed through a short silica gel column with n-hexane:diethyl ether (1: 1) as solvent to afford the pure product. The retrieved regent (4-hydroxypyridinesilica gel) was activated by treatment with 1.25 ml of concentrated HNO3 to provide 4-hydroxypyridinium nitrate SiO2, then reused for the oxidation.

References:

Ghalehbandi, Shermineh sadat;Ghazanfari, Dadkhoda;Ahmadi, Sayed Ali;Sheikhhosseini, Enayatollah [Organic Preparations and Procedures International,2021,vol. 53,# 2,p. 176 - 183]