3',4',5'-Trimethoxycinnamyl alcohol → 3-(3,4,5-Trimethoxyphenyl)Propan-1-Ol

HRID 1267623Notes

Reaction equation

HRID 1267623 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH2:15][OH:16])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]>C(O)C.[Pd]>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([CH2:13][CH2:14][CH2:15][OH:16])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 1

HCID 739243',4',5'-Trimethoxycinnamyl alcohol

Product 1

HCID 64288433-(3,4,5-Trimethoxyphenyl)Propan-1-Ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(3,4,5-Trimethoxyphenyl) -2-propen-1-ol (120 mg) was dissolved in ethanol, and to the solution 10% palladium on carbon (60 mg) was added, and the mixture was stirred at room temperature for 3 hours under a hydrogen atmosphere. The reaction mixture was filtered through celite, the filtrate was then concentrated under reduced pressure and extracted with chloroform. The resultant organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=14:1) to obtain the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was then concentrated under reduced pressure
  3. extractionextracted with chloroform
  4. washThe resultant organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=14:1)

Sources & evidence

ORD record
ord-a780be377630457893f2f3726ff7fcfa
Source dataset
uspto-grants-2003_04
Patent number
US06552188B2

Reaction notes

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