Perchloric Acid → HCID 13565969, compound

HRID 2290827Notes

Reaction equation

HRID 2290827 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:23](=O)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:32])[CH3:31])[CH:12]=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1.Cl(O)(=O)(=O)=O.[H][H]>C(O)C.[C].[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:32])[CH3:31])[CH:12]=[CH:13][C:14]=1[OH:15]

Participants

6

Reactant 3

HCID 24247Perchloric AcidHCID 13565961HCID 13565961, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13565969HCID 13565969, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Using 0.5 g of 10% palladium-carbon, 3.2 g of 1-(3,4-dibenzyloxyphenyl)-1,8-nonanedione was catalytically reduced in a mixture of 50 ml of ethanol and 1.5 ml of an aqueous 5% perchloric acid solution at room temperature and under atomospheric pressure until the absorption of hydrogen stopped. After the reaction was over, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was applied to silica gel (50 ml) column chromatography and eluted with a mixture of toluene and ethyl acetate (4:1). The crystals thus obtained were recrystallized from a mixture of toluene and n-hexane to provide 1-(3,4-dihydroxyphenyl)-8-nonanone.

Workup

  1. filtrationwas filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washeluted with a mixture of toluene and ethyl acetate (4:1)
  4. customThe crystals thus obtained
  5. customwere recrystallized from a mixture of toluene and n-hexane

Sources & evidence

ORD record
ord-3be415eb6f784c0fb2c7acfba74371e3
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

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