6-(4-Benzyloxyphenyl)-2,4-hexanedione → 6-(4-Hydroxyphenyl)-2,4-hexanedione

HRID 1868206Notes

Reaction equation

HRID 1868206 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](=[O:22])[CH2:18][C:19](=[O:21])[CH3:20])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].ClCCl>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17](=[O:22])[CH2:18][C:19](=[O:21])[CH3:20])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 597485826-(4-Benzyloxyphenyl)-2,4-hexanedioneHCID 178418361HCID 178418361, compound

Product 1

HCID 597485626-(4-Hydroxyphenyl)-2,4-hexanedioneYield 77.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

That is, 1.5 g of Pd-activated carbon (10%) was weighed in a nitrogen atmosphere and 20 ml of dichloromethane and 1.31 g (4.4 mmol) of 6-(4-benzyloxyphenyl)-2,4-hexanedione were added thereto. The atmosphere in the reaction system was exchanged with hydrogen at 1 atm and stirred at room temperature for 11 hours. The obtained reaction mixture was filtered to remove insoluble matter and the solvent was distilled off under reduced pressure. The residue was charged in a silica gel column and developed first with dichloromethane to remove byproducts. Subsequently, a solution containing a compound eluted from the column with a mixed solvent of 1:1 (by volume ratio) acetone/hexane was concentrated to dryness under reduced pressure to obtain 0.70 g (3.4 mmol) of the objective 6-(4-hydroxyphenyl)-2,4-hexanedione as pale yellow solid. Yield: 77%. Identification was performed by elementary analysis of C and H, and 1H-NMR.

Workup

  1. additionwere added
  2. customThe obtained reaction mixture
  3. filtrationwas filtered
  4. customto remove insoluble matter
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionThe residue was charged in a silica gel column
  7. customto remove byproducts
  8. additionSubsequently, a solution containing a compound
  9. washeluted from the column with a mixed solvent of 1:1 (by volume ratio) acetone/hexane
  10. concentrationwas concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b36eb101819945d4a4b465290f74f5c6
Source dataset
uspto-grants-2009_12
Patent number
US07635527B2

Reaction notes

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