ChemicalBook CAS DataBase List 4-Acetylbenzoic acid

4-Acetylbenzoic acid synthesis

12synthesis methods

Product Name:4-Acetylbenzoic acid
CAS Number:586-89-0
Molecular formula:C9H8O3
Molecular Weight:164.16

4-Acetylbenzoic acid is an intermediate for the preparation of curcumin analogs with antioxidant activity. It can be synthesized by the oxidation reaction of p-methylacetophenone and potassium permanganate to generate 4-acetylbenzoic acid, and then refluxing with anhydrous acetic acid for 1.5h.

122-00-9 Synthesis

122-00-9
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586-89-0
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Yield:586-89-0 92.1%

Reaction Conditions:

with carbon tetrabromide;oxygen in acetonitrile at 20; for 60 h;UV-irradiation;

Steps:

27 Example 27Compound 16
4-acetyltoluene (67 mg, 0.5 mmol),Carbon tetrabromide (16mg, 0.05mmol) was addedInto a reaction flask filled with oxygen,Plug in an oxygen balloon, and finally add 10ml of acetonitrile.Reaction at 400nm LED wavelength and room temperature for 60h,After the reaction, the solvent was distilled off under reduced pressure.Add excess 2mol / L sodium hydroxide solution for washing,Adjust the pH to about 10 ~ 11,The aqueous phase was extracted multiple times with ethyl acetate,Then add 2mol / L of dilute hydrochloric acid to the water phase,Adjust the pH to 1-2,The aqueous phase was extracted again with ethyl acetate several times,Evaporate the ethyl acetate and dry,That gives compound 16,The yield was 92.1%.

References:

Zhejiang University of Technology;Li Xiaoqing;Zheng Kun;Xu Xiangsheng CN110563571, 2019, A Location in patent:Paragraph 0158; 0159; 0160; 0161

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