Acetic Acid → 3-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester

HRID 1822343Notes

Reaction equation

HRID 1822343 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[CH3:22])=[CH:9][C:8]=1[CH3:23])[CH3:2].C(O)(=O)C.[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[CH3:22])=[CH:9][C:8]=1[CH3:23])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 690715883-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 578941493-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl esterYield 85.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-[4-(5-methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester (1.18 g, 3.63 mmol) and palladium under carbon (10%) (0.39 g, 0.36 mmol) in ethanol (20 mL) and acetic acid (2 mL) is stirred under 1 atm of hydrogen. After stirring overnight, the mixture is filtered off through Celite and washed with methanol. The mixture is concentrated under reduced pressure and purified by flash chromatography by eluting with hexane:ethyl acetate 5:1 to afford the title compound (1.02 g, 85%). Rf=0.42 (hexane:ethyl acetate 5:1). 1H NMR (300 MHz, CDCl3): δ1.26 (t, 3H, J=6.9 Hz), 2.16 (s, 3H), 2.28 (s, 3H), 2.56 (t, 2H, J=7.3 Hz), 2.90 (t, 2H, J=7.3 Hz), 3.72 (s, 3H), 4.17 (q, 2H, J=6.9 Hz), 6.45 (d, 1H, J=2.4 Hz), 6.62 (dd, 1H, J=2.8, 8.5 Hz), 6.67 (dd, 1H, J=2.4, 8.1 Hz), 6.74 (d, 1H, J=2.4 Hz), 7.06 (d, 1H, J=8.1 Hz), 7.13 (d, 1H, J=8.1 Hz).

Workup

  1. filtrationthe mixture is filtered off through Celite
  2. washwashed with methanol
  3. concentrationThe mixture is concentrated under reduced pressure
  4. custompurified by flash chromatography
  5. washby eluting with hexane:ethyl acetate 5:1

Sources & evidence

ORD record
ord-6ab7d7faceac4d55a972c9fae23f7c2b
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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