Methyl 4-methylsalicylate Chemical Properties

Melting point:

27-28℃

Boiling point:

242 °C

Density 

1.147

refractive index 

1.5370

Flash point:

28 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Low Melting Solid

pka

9.87±0.10(Predicted)

color 

Pale brown to pale yellow

FreezingPoint 

24.0 to 28.0 ℃

InChI

InChI=1S/C9H10O3/c1-6-3-4-7(8(10)5-6)9(11)12-2/h3-5,10H,1-2H3

InChIKey

UITFCFWKYAOJEJ-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(C)C=C1O

LogP

3.000 (est)

CAS DataBase Reference

4670-56-8(CAS DataBase Reference)

Safety Information

HS Code 

2918230000

Methyl 4-methylsalicylate Usage And Synthesis

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 3534, 1980 DOI: 10.1021/ja00530a038

Synthesis

Step 1: 3-hydroxy-4-methylbenzoic acid (4.56 g, 30 mmol) was dissolved in methanol (60 mL) and thionyl chloride (40 drops) was added slowly and dropwise. The reaction mixture was heated to reflux and maintained for 18 hours. Upon completion of the reaction, the volatile components were removed by distillation under reduced pressure. The crude product was purified by fast column chromatography on silica gel, using gradient elution with ethyl acetate/heptane (2%-40%) to afford methyl 2-hydroxy-4-methylbenzoate (3.04 g, 61% yield) as a colorless oil. Mass spectrometry analysis (ESI/APCI+): m/z 167 ([M-H]-).

References

[1] Patent: WO2010/130842, 2010, A1. Location in patent: Page/Page column 132-133

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