Ethyl 4-hydroxyphenylacetate Chemical Properties

Melting point:

36-38°C

Boiling point:

187-189°C 20mm

Density 

1.146±0.06 g/cm3(Predicted)

refractive index 

1.52

Flash point:

187-189°C/20mm

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform

form 

Brown Semi-Solid

pka

9.84±0.15(Predicted)

color 

White or Colorless to Light yellow

LogP

1.760 (est)

CAS DataBase Reference

17138-28-2(CAS DataBase Reference)

NIST Chemistry Reference

Benzeneacetic acid, 4-hydroxy-, ethyl ester(17138-28-2)

EPA Substance Registry System

Benzeneacetic acid, 4-hydroxy-, ethyl ester (17138-28-2)

Safety Information

Safety Statements 

22-24/25

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

2916340000

MSDS

• Language:English Provider:ALFA

Ethyl 4-hydroxyphenylacetate Usage And Synthesis

Chemical Properties

Brown Semi-Solid

Uses

Ethyl 4-hydroxyphenylacetate is a useful synthetic intermediate for the preparation of novel antiinflammatory agents.

Synthesis

4-Hydroxyphenylacetic acid (10.0 g, 65.7 mmol), anhydrous ethanol (120 mL), and concentrated hydrochloric acid (1 mL) were added to a round bottom flask. The reaction mixture was heated to reflux for 1 h and subsequently cooled to room temperature. The reaction mixture was neutralized in a small amount with saturated aqueous sodium bicarbonate solution. Most of the ethanol was evaporated under reduced pressure. The aqueous phase was extracted with ethyl acetate and the organic phase was sequentially washed well with water and dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the target product ethyl p-hydroxyphenylacetate as an oil (11.8 g, 100% yield). The product was confirmed by NMR hydrogen spectrum (400 MHz, CDCl3): δ 7.13 (d, 2H), 6.76 (d, 2H), 5.10 (s, 1H), 4.15 (q, 2H), 3.36 (s, 2H), 1.26 (t, 3H).

target

MAO

References

[1] Patent: WO2006/20916, 2006, A2. Location in patent: Page/Page column 79
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 22, p. 8092 - 8105
[3] Synthesis, 2003, # 16, p. 2479 - 2482
[4] Patent: US2003/191181, 2003, A1. Location in patent: Page/Page column 10; 15
[5] Journal of Medicinal Chemistry, 1988, vol. 31, # 8, p. 1651 - 1656

Ethyl 4-hydroxyphenylacetate(17138-28-2)Related Product Information

• 4-Hydroxybenzoic acid
• Ethyl phenylacetate
• p-(2-Methoxyethyl) phenol
• Trinexapac-ethyl
• 4-Hydroxybenzaldehyde
• Sodium 4-hydroxybenzenesulfonate
• ISOXADIFEN-ETHYL
• Ethyl cyanoacetate
• 4-Methoxyphenol
• 4-Hydroxyphenylacetic acid
• Ethyl pyruvate
• Ethylparaben
• Methylparaben
• 3,4-Dihydroxyphenylacetic acid
• Ethyl acrylate
• 2-(4-HYDROXYPHENYL)ACETALDEHYDE
• 2-Hydroxyphenylacetic acid
• 4-HYDROXYBENZOIC ACID N-AMYL ESTER