METHYL 5-METHOXYSALICYLATE Chemical Properties

Boiling point:

235-240 °C (lit.)

Density 

1.223 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.544(lit.)

Flash point:

>230 °F

storage temp. 

Storage temp. 2-8°C

pka

10.24±0.18(Predicted)

form 

clear liquid

color 

Colorless to Light yellow

λmax

334nm(CH3CN)(lit.)

CAS DataBase Reference

2905-82-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2918999090

MSDS

• Language:English Provider:SigmaAldrich

METHYL 5-METHOXYSALICYLATE Usage And Synthesis

Synthesis

To a solution of N,N-dimethylformamide (80 mL) of 2-hydroxy-5-methoxybenzoic acid (6.0 g, 35.68 mmol) was sequentially added sodium bicarbonate (3.15 g, 37.46 mmol) and iodomethane (2.33 mL, 37.46 mmol). The reaction mixture was stirred at 80 °C for 3 hours. Upon completion of the reaction, ice water was added to the mixture, followed by extraction with ether. The combined organic phases were washed sequentially with water and saturated brine and then dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give the brown oily product methyl 2-hydroxy-5-methoxybenzoate (5.38 g, 82.8% yield).

References

[1] Patent: US2004/242615, 2004, A1. Location in patent: Page/Page column 13
[2] ChemMedChem, 2016, vol. 11, # 1, p. 108 - 118
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 2, p. 334 - 343
[4] Organic Letters, 2018, vol. 20, # 5, p. 1316 - 1319

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