Dehydroparadol → Paradol

HRID 2093245Notes

Reaction equation

HRID 2093245 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10](=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=1[O:19][CH3:20].[H][H]>C(O)C.[C].[Pd]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=1[O:19][CH3:20]

Participants

5

Reactant 2

HCID 6438480DehydroparadolHCID 178418361HCID 178418361, compound

Product 1

HCID 94378ParadolYield 58%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Moreover, 10 g (36 mmol) of the resulting (E)-1-(4′-hydroxy-3′-methoxyphenyl)dec-1-en-3-one was dissolved in 100 mL of ethanol followed by the addition of 1 g of palladium carbon (5% palladium) to this solution and stirring overnight at normal temperature in a hydrogen atmosphere (normal pressure). After filtering the insoluble matter, the filtrate was concentrated under reduced pressure to obtain 9.8 g of crude product. This crude product was purified by column chromatography (SiO2/CHCl3) to obtain 1-(4′-hydroxy-3′-methoxyphenyl)-3-decanone (5.6 g, yield: 58%).

Workup

  1. filtrationAfter filtering the insoluble matter
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto obtain 9.8 g of crude product
  4. customThis crude product was purified by column chromatography (SiO2/CHCl3)

Sources & evidence

ORD record
ord-2b2be620f44e42509f6ccd378fe02456
Source dataset
uspto-grants-2013_05
Patent number
US08445005B2

Reaction notes

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