3-(3,5-Dimethoxyphenyl)propanoic acid is a derivative of 3-(3,4-Dimethoxyphenyl)propanoic Acid (D460730), which is one of the novel circulating coffee metabolites in human plasma.
General procedure for the synthesis of 3,5-dimethoxyphenylpropionic acid from (E)-3-(3,5-dimethoxyphenyl)propenoic acid: to a mixed solution of (E)-3-(3,5-dimethoxyphenyl)propenoic acid (12 g, 57.7 mmol) in ethyl acetate (EtOAc, 100 ml) and methanol (MeOH, 100 ml), 10% palladium/carbon ( Pd/C, 1.3 g). The reaction mixture was placed in a Parr apparatus and the reaction was shaken under 30-40 psi hydrogen pressure for 5 hours. Upon completion of the reaction, the reaction solution was filtered through a diatomaceous earth pad and the filtrate was collected. The filtrate was concentrated and dried under reduced pressure at 50 °C to afford the target product 3,5-dimethoxyphenylpropionic acid (11.7 g, 96.55% yield). m/e 209 (M-1) by LC-MS.
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