Reaktion #44325

Reaktionsgleichung

6-(4-benzyloxyphenyl)-2,4-hexanedione

hydrogen

→

6-(4-hydroxyphenyl)-2,4-hexanedione

Ausbeute 77.3%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   SonstigeThe obtained reaction mixture
3. 3
   Filtrationwas filtered
4. 4
   Sonstigeto remove insoluble matter
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
6. 6
   workup.ADDITIONThe residue was charged in a silica gel column
7. 7
   Sonstigeto remove byproducts
8. 8
   workup.ADDITIONSubsequently, a solution containing a compound
9. 9
   Wascheneluted from the column with a mixed solvent of 1:1 (by volume ratio) acetone/hexane
10. 10
    Einengenwas concentrated to dryness under reduced pressure

Vorschrift

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.

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