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

HRID 1515010Notes

Reaction equation

HRID 1515010 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

To a solution of 3-(4-formyl-3,5-dimethylphenyl)-acrylic acid methyl ester (900 mg, 4.1 mmol) in CH2Cl2 (20 mL) was added 10% Pd/C (90 mg) and the mixture was hydrogenated at one atm overnight. The catalyst was filtered through Celite and was washed with CH2Cl2. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (5:1) to give 3-(4-formyl-3,5-dimethylphenyl)-propionic acid methyl ester as a light yellow oil.

Workup

  1. customwas hydrogenated at one atm overnight
  2. filtrationThe catalyst was filtered through Celite
  3. washwas washed with CH2Cl2
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-25ad98892efe4502b9bc76a4f9bfb1dc
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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