3-(4-Methoxyphenyl)-2-phenylprop-2-enoic acid → 3-(4-Methoxyphenyl)-2-phenylpropionic acid

HRID 1455037

Reaction equation

HRID 1455037 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([OH:13])=[O:12])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 2366983-(4-Methoxyphenyl)-2-phenylprop-2-enoic acid

Product 1

HCID 977393-(4-Methoxyphenyl)-2-phenylpropionic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

13 g of 3-(4-methoxyphenyl)-2-phenylacrylic acid was dissolved to 600 ml of ethyl acetate and 2.6 g of 10% palladium on charcoal was added under inert atmosphere. Starting material was hydrogenated at room temperature to give quantitative yield of 3-(4-methoxyphenyl)-2-phenylpropionic acid. 1H-NMR (400 MHz, d6-DMSO): 12.3 (bs, 1H), 7.32-7.20 (m, 5H), 7.1-7.0 (m, 2H), 6.8-6.7 (m, 2H), 3.79 (dd, 1H, J 6.9, 8.7 Hz), 3.70 (s, 3H), 3.22 (dd, 1H, J 8.7, 13.7 Hz), 2.87 (dd, 1H, J 6.9, 13.7 Hz).

Workup

  1. additionwas added under inert atmosphere
  2. customwas hydrogenated at room temperature

Sources & evidence

ORD record
ord-d26138cc3e07439a8cf2565f7ab0f9bc
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Linked notes

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