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

HRID 1360774Notes

Reaction equation

HRID 1360774 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-04b89f881d994a98989643dc8f93b84a
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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