3-(4-Formyl-3,5-dimethylphenyl)-acrylic acid methyl ester → Methyl 3-(3,5-dimethyl-4-formylphenyl)propionate

HRID 1513270Notes

Reaction equation

HRID 1513270 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH:13]=[O:14])=[C:8]([CH3:15])[CH:7]=1>C(Cl)Cl.[Pd]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH:13]=[O:14])=[C:8]([CH3:15])[CH:7]=1

Participants

4

Reactant 1

HCID 866328203-(4-Formyl-3,5-dimethylphenyl)-acrylic acid methyl ester

Product 1

HCID 54209618Methyl 3-(3,5-dimethyl-4-formylphenyl)propionate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(4-formyl-3,5-dimethylphenyl)-acrylic acid methyl ester (900 mg, 4.1 mmol) and 10% Pd/C (90 mg) in CH2Cl2 (20 mL) was hydrogenated at one atm overnight. The catalyst was filtered through Celite and washed with CH2Cl2. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (heptane/EtOAc=5:1) to give the title compound. MS: m/z 221 (M+1).

Workup

  1. customwas hydrogenated at one atm overnight
  2. filtrationThe catalyst was filtered through Celite
  3. washwashed with CH2Cl2
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by flash chromatography (heptane/EtOAc=5:1)

Sources & evidence

ORD record
ord-b0b8b8e397c847639983b02383f8f940
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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