3-(4-Methylbenzoyl)propionic acid Chemical Properties

Melting point:

127-130 °C(lit.)

Boiling point:

288.19°C (rough estimate)

Density 

1.1430 (rough estimate)

refractive index 

1.5340 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

4.57±0.17(Predicted)

color 

White to Almost white

Water Solubility 

insoluble

BRN 

2099653

CAS DataBase Reference

4619-20-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2915601990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-(4-Methylbenzoyl)propionic acid Usage And Synthesis

Chemical Properties

White to light beige crystalline powder

Uses

3-(4-Methylbenzoyl)propionic acid can be used as an intermediate in agrochemical, pharmaceutical and dyestuff field

General Description

4-(4-Methylphenyl)-4-oxobutyric acid is an organic building block. It is a commercial corrosion inhibitor.

Synthesis

The general procedure for the synthesis of 3-(4-methylbenzoyl)propionic acid from succinic anhydride and toluene was as follows: 75.7 g of succinic anhydride was dissolved in 457.5 mL of toluene. Under stirring, 220.5 g of anhydrous aluminum trichloride (AlCl3) was added in batches. The temperature of the reaction mixture was maintained in the range of 50-60 °C. After 2 hours of reaction, the completion of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was slowly added dropwise to 1250 mL of 1 mol/L ice hydrochloric acid under vigorous stirring. During the dropwise addition, milky solids were gradually precipitated. After completion of the dropwise addition, the mixture was continued to be stirred for 0.5 h, followed by filtration. The filter cake was washed sequentially with toluene and ice water and then pumped with 50 mL of ethyl acetate. The resulting solution was slowly added to 500 mL of petroleum ether to induce crystallization. After stirring for 0.5 h, the crystals were collected by filtration and dried at 40 °C for 2 h to give 144 g of Compound II (intermediate) in 99.3% yield. [Compound II intermediate] was a white solid.

References

[1] Organic Letters, 2016, vol. 18, # 3, p. 504 - 507
[2] Patent: CN107628947, 2018, A. Location in patent: Paragraph 0053; 0054; 0055; 0056; 0057
[3] Russian Journal of General Chemistry, 2014, vol. 84, # 9, p. 1825 - 1829
[4] Zhurnal Obshchei Khimii, 2014, vol. 84, # 9, p. 1825 - 1829,5
[5] Molecules, 2018, vol. 23, # 3,

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