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METHYL 4-ACETYLBENZOATE-Application

Dec 12，2019

Methyl 4-acetylbenzoate(C10H10O3) is white to off-white solid. Methyl 4-acetylbenzoate is an aromatic ketone that can be prepared from 4-bromoacetophenone. Methyl 4-acetylbenzoate may be used in the preparation of 4-methoxycarbonyl-α-oxo-benzeneacetic acid and methyl 4-(2-(2-methylimidazo[1,2-a]pyridin-3-yl)-2-oxoacetyl)benzoate. Methyl 4-Acetylbenzoate is used in the preparation of trisubstituted pyrazoles as novel hepatitis C virus entry inhibitors[1].

Article illustration
Fig 1. Chemical structure formula and three-dimensional structure

Preparation

Adding 98g (0.6mol) of methyl p-ethylbenzoate(2), 1g of chromium oxide and 4g of calcium carbonate to the mortar, and grinding it into a reaction bottle equipped with a stirrer, a thermometer and a ventilation duct. Heating the reaction flask by introducing air. Heat to 140-150°C with vigorous stirring, and react for 24 h. The water produced is continuously distilled and collected throughout the process. After completion of the reaction, 100 mL of benzene was added, filtered, and the filter cake was washed with benzene. Distilling under reduced pressure, recovering unreacted raw material(2) 29-32g (118-121°C/2.13kPa), and then collecting fractions of 149-150°C/0.93kPa to obtain compound(1) 43-45g, conversion rate 40%～42%, yield 60%. Recrystallization from benzene-hexane (1:1) gave a white solid, mp 92-94°C[2].

Article illustration

4-(5-methyl-diazolyl) -phenyl-1,3-butanedione was synthesized by dehydration reaction with methyl 4-acetylbenzoate and hydrazine hydrate as raw materials.

Methyl 4-acetylbenzoate is an important chemical raw material, intermediates for organic synthesis, fine chemicals, and intermediates for drug development. In the previous reaction to synthesize para-ethyl benzoate, p-acetyl iodinated benzene or para-ethyl bromobenzene was used as the raw material, and under the action of the catalyst, Methyl 4-acetylbenzoate was formed[3,4].

References

[1] Hwang, J.Y., et al.: Bioorg. Med. Chem. Lett., 23, 6467 (2013).
[2] William S Emerson and George F Deebel.Org Synth,1963,Coll Vol 4:579.
[3] Abu-Reziq,R. Wang,D.S. Post, M. Alper, H. Chem.Mater.2008,20,2544.
[4] Liu, S. Berry,N. Thomoson,N. Pettman,A. Hyder, Z. Mo,J. Xiao, J. J.Org.Chem. 2006,71,7467.

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