3,5-Dimethyl-4-methoxybenzoic acid Chemical Properties

Melting point:

191-195 °C (lit.)

Boiling point:

253.02°C (rough estimate)

Density 

1.1185 (rough estimate)

refractive index 

1.5392 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

4.61±0.10(Predicted)

form 

Crystalline Solid

color 

White to brown

CAS DataBase Reference

21553-46-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26-36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

6.1

HS Code 

29189900

MSDS

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3,5-Dimethyl-4-methoxybenzoic acid Usage And Synthesis

Chemical Properties

white to brown crystalline solid

Synthesis

General procedure for the synthesis of 3,5-dimethyl-4-methoxybenzoic acid from 4-methoxy-3,5-dimethylbenzenecarbonitrile: 4-methoxy-3,5-dimethylbenzenecarbonitrile (1664 mg) was suspended in ethanol (32 mL), to which 8M NaOH solution (163 mL) was added. The mixture was placed in a pressure reactor and the reaction was stirred at 120 °C overnight. Upon completion of the reaction, ethanol was removed by rotary evaporation. Water was added to the residue and the aqueous solution was washed with ether to remove non-polar impurities. Subsequently, the aqueous layer was acidified with concentrated hydrochloric acid to pH < 2, at which point the target product precipitated as a solid. The acidified aqueous layer was extracted with ethyl acetate and the organic phases were combined and washed sequentially with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to afford 3,5-dimethyl-4-methoxybenzoic acid as a white solid in 99% yield.LRMS (m/z): 181 ([M+H]+).HPLC retention time: 5.52 min (Method B).

References

[1] Patent: WO2011/144338, 2011, A1. Location in patent: Page/Page column 92
[2] Patent: EP2390252, 2011, A1. Location in patent: Paragraph 0449; 0450

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