HCID 11788723, compound → 3-(4-Methoxyphenyl)cyclopentan-1-one

HRID 1108766Notes

Reaction equation

HRID 1108766 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=2)=[CH:5][CH:4]=1.[H][H]>C(O)C.[C].[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 11788723HCID 11788723, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 140909103-(4-Methoxyphenyl)cyclopentan-1-oneYield 52.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

3-(4-Methoxyphenyl)-2-cyclopenten-1-one (11.2 g) was dissolved in ethanol, and 10% palladium-carbon (1.1 g) was added thereto. After substituting the reaction vessel with hydrogen gas, hydrogen addition was carried out at normal pressure, 40° C. for 4 hours. After the reaction, the catalyst was filtered off and the solvent was distilled off under reduced pressure to produce a light yellow oily substance which was then purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to give 5.90 g of 3-(4-methoxyphenyl) cyclopentanone (52.2% yield).

Workup

  1. customAfter the reaction
  2. filtrationthe catalyst was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. customto produce a light yellow oily substance which
  5. customwas then purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-2b3530feb5744c4a85f1f369243d2880
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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