4-HYDROXY-2-METHYLBENZOIC ACID 98 Chemical Properties

Melting point:

177-181 °C

Boiling point:

339.1±30.0 °C(Predicted)

Density 

1.304±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.46±0.25(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C8H8O3/c1-5-4-6(9)2-3-7(5)8(10)11/h2-4,9H,1H3,(H,10,11)

InChIKey

BBMFSGOFUHEVNP-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(O)C=C1C

CAS DataBase Reference

578-39-2

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

2

HS Code 

29182900

4-HYDROXY-2-METHYLBENZOIC ACID 98 Usage And Synthesis

Chemical Properties

White or pink crystalline powder

Definition

ChEBI: 4-hydroxy-2-methylbenzoic acid is a hydroxybenzoic acid.

Synthesis

General procedure for the synthesis of 4-hydroxy-2-methylbenzoic acid from 4-methoxy-2-methylbenzoic acid: boron tribromide (20 mmol, 5 g, 10 eq.) was slowly added to a solution of 4-methoxy-2-methylbenzoic acid (2 mmol, 0.332 g) in dichloromethane (20 mL) under argon protection. The reaction mixture was stirred at room temperature until high performance liquid chromatography (HPLC) analysis showed complete consumption of the feedstock. Subsequently, 0.1 M hydrochloric acid (20 mL) was added to the reaction system to quench the reaction and the insoluble material was removed by filtration. The aqueous phase was concentrated under reduced pressure and the residue was dissolved in methanol and concentrated again under reduced pressure to remove the solvent. This dissolution-concentration process was repeated three times, resulting in purified 4-hydroxy-2-methylbenzoic acid as a yellow solid (0.24 g, 80% yield).

References

[1] European Journal of Organic Chemistry, 2008, # 5, p. 816 - 825
[2] Patent: WO2006/64286, 2006, A1. Location in patent: Page/Page column 93-94
[3] Patent: WO2007/144379, 2007, A1. Location in patent: Page/Page column 39
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, p. 679 - 682
[5] Patent: WO2006/79099, 2006, A2. Location in patent: Page/Page column 68; 69

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