METHYL 2-CHLORO-5-HYDROXYBENZOATE Chemical Properties

Boiling point:

320.1±22.0 °C(Predicted)

Density 

1.354±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

8.70±0.18(Predicted)

form 

solid

color 

Grey-yellow

Safety Information

HS Code 

2918290090

METHYL 2-CHLORO-5-HYDROXYBENZOATE Usage And Synthesis

Synthesis

To a solution of 2-chloro-5-hydroxybenzoic acid (4 g, 23.6 mmol) in methanol (50 mL) cooled to 0 °C was added thionyl chloride (2.5 mL, 35 mmol) dropwise. The reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure and the residue was dissolved in ethyl acetate (100 mL). The organic phase was washed sequentially with saturated sodium bicarbonate solution (3 x 50 mL), water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The product was white crystals in 99% yield, melting point 96-97 °C. 1H NMR (400 MHz, CDCl3) δ: 3.91 (s, 3H, OCH3), 6.91 (dd, J=8.7, 3.1 Hz, 1H, Ar-H), 7.27 (d, J=8.7 Hz, 1H, Ar-H), 7.31 (d, J=3.1 Hz, 1H Ar-H).13C NMR (100MHz, CDCl3) δ: 52.79, 118.15, 120.33, 124.67, 130.25, 132.14, 154.51, 166.77.ESI HRMS Calculated value [M+H]+: 187.0162, Measured value: 187.0155.HPLC retention Time tR = 10.618 min (100% detection at both 220 nm and 254 nm).

References

[1] European Journal of Medicinal Chemistry, 2014, vol. 73, p. 83 - 96
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3141 - 3147
[3] Gazzetta Chimica Italiana, 1899, vol. 29 I, p. 376
[4] Patent: WO2012/114268, 2012, A1. Location in patent: Page/Page column 119-120
[5] Patent: US2014/73651, 2014, A1. Location in patent: Paragraph 0879; 0880

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