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ChemicalBook CAS DataBase List 3-(4-Hydroxymethyl-phenyl)-propionic acid ethyl ester
107859-98-3

3-(4-Hydroxymethyl-phenyl)-propionic acid ethyl ester synthesis

5synthesis methods
3-(4-FORMYLPHENYL)-2-PROPENOIC ACID ETHYL ESTER

51828-89-8

3-(4-HYDROXYMETHYL-PHENYL)-PROPIONIC ACID ETHYL ESTER

107859-98-3

(B) A mixture of ethyl (E)-3-(4-formylphenyl)acrylate (2 g, 9.79 mmol), Pd/C (1 g, 10 wt%), and ethanol (50 mL) was placed in an autoclave reactor and hydrogenated for 2 h at 3.5 atm hydrogen pressure. Upon completion of the reaction, the catalyst was removed by filtration. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: 0-15% ethyl acetate/petroleum ether) to afford ethyl 3-(4-(hydroxymethyl)phenyl)propionate (1.54 g, 76% yield) as a colorless liquid.LC/MS analysis: calculated value (C12H16O3) 208.25, measured value 191.0 [M-OH] +.

-

Yield:-

Steps:

Multi-step reaction with 2 steps
1: tris-(o-tolyl)phosphine; palladium diacetate; triethylamine / N,N-dimethyl-formamide / 100 °C / Inert atmosphere; Sealed tube
2: hydrogen; palladium 10% on activated carbon / ethanol / 2 h / 2660.18 Torr

References:

JANSSEN PHARMACEUTICA NV;KUO, Gee-Hong;PLAYER, Mark R.;YANG, Shyh-Ming;ZHANG, Yue-Mie;HUANG, Hui WO2016/57731, 2016, A1