3-HYDROXYPHENYLACETIC ACID METHYL ESTER Chemical Properties

Boiling point:

146°C/14mmHg(lit.)

Density 

1.181±0.06 g/cm3(Predicted)

refractive index 

1.5340 to 1.5380

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Oil

pka

9.61±0.10(Predicted)

color 

Clear Colourless to Clear Pale Yellow

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2918290090

3-HYDROXYPHENYLACETIC ACID METHYL ESTER Usage And Synthesis

Uses

Methyl 3-Hydroxyphenylacetate is a phenylacetic acid derivative and a CRTH2 and DP dual antagonist.

Synthesis

Step 1: 3-Hydroxyphenylacetic acid (15.2 g, 0.1 mol, 1.0 eq.) and concentrated sulfuric acid (392 mg, 4 mmol, 0.04 eq.) were dissolved in methanol (100 mL). The reaction mixture was stirred at room temperature for 1 h. The reaction was subsequently quenched with sodium hydroxide solution. The reaction mixture was extracted with ethyl acetate and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=5:1) to afford methyl 2-(3-hydroxyphenyl)acetate as a yellow oil (14.2 g, 86% yield).1H NMR (400 MHz, CDCl3) δ= 7.15-7.19 (m, 1H), 6.81 (d, 1H), 6.72-6.76 (m, 2H), 5.88 (m, 2H). 2H), 5.88 (s, 1H), 3.70 (s, 3H), 3.58 (s, 2H); LCMS m/z 167 [M + 1]+.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 21, p. 5488 - 5492
[2] Patent: WO2004/63155, 2004, A1. Location in patent: Page 58
[3] Patent: WO2005/66136, 2005, A1. Location in patent: Page/Page column 51
[4] Patent: WO2005/19190, 2005, A2. Location in patent: Page/Page column 51
[5] Patent: WO2005/103050, 2005, A2. Location in patent: Page/Page column 168

3-HYDROXYPHENYLACETIC ACID METHYL ESTER(42058-59-3)Related Product Information

• Methyl 3,5-dihydroxyphenylacetate
• METHYL HOMOVERATRATE
• 3-Methoxyphenylacetic acid
• ETHYL HOMOVANILLATE
• 3-HYDROXYPHENYLACETIC ACID METHYL ESTER
• RESINIFERATOXIN
• ETHYL 3-METHOXYPHENYLACETATE
• NOGALAMYCIN
• ACLARUBICIN HYDROCHLORIDE
• (2-HYDROXY-PHENYL)-ACETIC ACID METHYL ESTER
• Methyl cyclohexylphenylglycolate
• METHYL 2-AMINO-2-(4-HYDROXYPHENYL)ACETATE
• 4-HYDROXYPHENYLACETIC ACID METHYL ESTER,p-Hydroxyphenylacetic acid methyl ester
• methyl 2-(3-amino-4-hydroxyphenyl)acetate
• alpha-Hydroxyphenylacetic acid methyl ester,rac-(R*)-Hydroxyphenylacetic acid methyl ester
• 3,4-DIHYDROXYPHENYLACETIC ACID METHYL ESTER
• Methyl cyclopentylphenylglycolate
• (S)-(+)-ALPHA-HYDROXYPHENYLACETIC ACID METHYL ESTER,(s)-(+)-à-hydroxyphenylacetic acid methyl ester