3-HYDROXY-5-METHYL-BENZOIC ACID

3-HYDROXY-5-METHYL-BENZOIC ACID Property

Melting point:

210°C

Boiling point:

234.6°C (rough estimate)

Density 

1.2143 (rough estimate)

refractive index 

1.4945 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

pka

4.15±0.10(Predicted)

Appearance

Light yellow to brown Solid

Safety

HS Code 

2916399090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

3-HYDROXY-5-METHYL-BENZOIC ACID Chemical Properties,Usage,Production

Chemical Properties

White powder

Uses

3,5-Cresotic Acid is a reactant used in the preparation of trisubstituted benzenes as thrombin inhibitors for the treatment of coagulation disorders.

Synthesis

General procedure for the synthesis of 3-hydroxy-5-methylbenzoic acid from the compound (CAS:100118-65-8): the oxo compound (57 g, 0.21 mol) was added to water (450 mL) together with magnesium oxide (38.1 g, 0.945 mol). The reaction mixture immediately changed to a dark reddish-orange color, followed by a gradual change to a light brown color over about 15 minutes. After continuous stirring and heating for 30 minutes, the excess magnesium oxalate and magnesium oxide were removed by filtration. The residue was washed with warm water, the filtrates were combined and concentrated by distillation under vacuum to about 30 mL. The concentrate was slowly added to a mixture consisting of concentrated hydrochloric acid and water (1:1, v/v, 50 mL), whereupon a precipitate was produced. The precipitate was filtered, washed with cold water and dried. Finally, purification by recrystallization in water afforded 3-hydroxy-5-methylbenzoic acid as a light brown solid (13.43 g, 42% yield). Melting point: 202-203 °C (literature value 207-208 °C); 1H NMR (D2O) δ: 2.19 (s, 3H), 6.82 (s, 1H), 7.07 (s, 1H), 7.20 (s, 1H); 13C NMR (D2O) δ: 20.20, 113.00, 121.03, 122.25, 130.65, 140.55, 155.34, 170.26.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 16, p. 4720 - 4723
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 19, p. 5622 - 5626
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 11, p. 3961 - 3973
[4] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 7, p. 1848 - 1858
[5] Patent: US2011/15395, 2011, A1. Location in patent: Page/Page column 13