6-(4-Hydroxyphenyl)hex-5-ene-2,4-dione → 6-(4-Hydroxyphenyl)-2,4-hexanedione

HRID 1040383Notes

Reaction equation

HRID 1040383 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:15])[CH2:11][C:12](=[O:14])[CH3:13])=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10](=[O:15])[CH2:11][C:12](=[O:14])[CH3:13])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 671067346-(4-Hydroxyphenyl)hex-5-ene-2,4-dione

Product 1

HCID 597485626-(4-Hydroxyphenyl)-2,4-hexanedioneYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(4-hydroxyphenyl)hex-5-ene-2,4-dione (1.00 g, 4.90 mmol) in 50 mL of ethyl acetate was added palladium 5% on carbon (200 mg) under nitrogen. After the vessel was purged with hydrogen, the reaction mixture was stirred under 1 atm of hydrogen at room temperature for 12 h. After the vessel was purged with nitrogen, the reaction mixture was filtered to remove palladium 5% on carbon. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 60/40) to obtain the title compound as a colorless oil (802 mg, 80%) having the following characteristics.

Workup

  1. customAfter the vessel was purged with hydrogen
  2. customAfter the vessel was purged with nitrogen
  3. filtrationthe reaction mixture was filtered
  4. customto remove palladium 5% on carbon
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=70/30 to 60/40)

Sources & evidence

ORD record
ord-d627775ff6294b91b05e231fd36264e9
Source dataset
uspto-grants-2013_10
Patent number
US08552220B2

Reaction notes

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