ethyl 3-hydroxyphenylacetate Chemical Properties

Boiling point:

179°C/12mmHg(lit.)

Density 

1.146±0.06 g/cm3(Predicted)

refractive index 

1.5220 to 1.5270

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Dichloromethane, Ethyl Acetate, Toluene

pka

9.75±0.10(Predicted)

form 

clear liquid

color 

Light yellow to Yellow to Orange

Stability:

Store in Freezer

Safety Information

HS Code 

2918290090

ethyl 3-hydroxyphenylacetate Usage And Synthesis

Chemical Properties

Light Yellow Liquid

Uses

Ethyl 3-hydroxyphenylacetate is a useful synthetic intermediate for the preparation of novel antiinflammatory agents.

Synthesis

General procedure for the synthesis of ethyl 2-(3-hydroxyphenyl)acetate (S16-2) from ethanol and 3-hydroxyphenylacetic acid: 8 mL of concentrated sulfuric acid was added to a 200 mL ethanol solution of 3-hydroxyphenylacetic acid (S16-1; 10 g, 65.8 mmol). The reaction mixture was heated to reflux overnight. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with distilled water. The organic layers were combined, washed with saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by evaporation to give the crude product. The crude product was purified by fast column chromatography to afford the target compound S16-2 in colorless oily form in quantitative yield. The structure of the product was confirmed by 1H NMR (500 MHz, CDCl3): δ 7.35 (br, 1H), 7.12 (m, 1H), 6.69-6.78 (m, 3H), 4.12 (m, 2H), 3.53 (s, 2H), 1.21 (m, 3H).

References

[1] Patent: WO2007/56366, 2007, A2. Location in patent: Page/Page column 26
[2] Patent: WO2007/56497, 2007, A1. Location in patent: Page/Page column 22
[3] Patent: WO2011/44394, 2011, A1. Location in patent: Page/Page column 127-128
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 14, p. 6427 - 6437
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 299 - 302

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