反応 #44325

反応方程式

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

hydrogen

→

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

収率 77.3%

溶媒

dichloromethane

反応条件

後処理

1. 1
   workup.ADDITIONwere added
2. 2
   その他The obtained reaction mixture
3. 3
   ろ過was filtered
4. 4
   その他to 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
   その他to remove byproducts
8. 8
   workup.ADDITIONSubsequently, a solution containing a compound
9. 9
   洗浄eluted from the column with a mixed solvent of 1:1 (by volume ratio) acetone/hexane
10. 10
    濃縮was concentrated to dryness under reduced pressure

実験手順

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.

出典