Methyl 4-hydroxy-3-methylbenzoate Chemical Properties

Melting point:

124-125℃

Boiling point:

282.9±20.0 °C(Predicted)

Density 

1.169±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

8.70±0.18(Predicted)

Appearance

Light brown to off-white Solid

Safety Information

HS Code 

2918290090

Methyl 4-hydroxy-3-methylbenzoate Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 3-methyl-4-hydroxybenzoate from methanol and 4-hydroxy-3-methylbenzoic acid: 4-hydroxy-3-methylbenzoic acid (342 g, 2.24 mol) was dissolved in methanol (3.5 L), and the solution was bubbled with hydrogen chloride gas (HCl) for 5 min. Subsequently, the reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the reaction mixture was concentrated to afford methyl 3-methyl-4-hydroxybenzoate (372 g, quantitative yield). NMR hydrogen spectrum of the product (1H-NMR, CDCl3, δ ppm): 7.82 (1H, single peak), 7.78 (1H, double peak), 6.80 (1H, double peak), 3.86 (3H, single peak), 2.22 (3H, single peak).

References

[1] Patent: WO2003/101978, 2003, A1. Location in patent: Page 170-171
[2] European Journal of Medicinal Chemistry, 2009, vol. 44, # 7, p. 2994 - 3008
[3] Patent: US2006/135484, 2006, A1. Location in patent: Page/Page column 59
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 7, p. 3059 - 3075
[5] Patent: WO2012/125613, 2012, A1. Location in patent: Page/Page column 146

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