HCID 54067867, compound → HCID 19744878, compound

HRID 2254277Notes

Reaction equation

HRID 2254277 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25]CC3C=CC=CC=3)=[C:21]([CH2:33][CH:34]=[C:35]([CH3:37])[CH3:36])[C:20]=2[OH:38])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C>[OH:38][C:20]1[C:21]([CH2:33][CH2:34][CH:35]([CH3:36])[CH3:37])=[C:22]([OH:25])[CH:23]=[CH:24][C:19]=1[C:17](=[O:18])[CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 54067867HCID 54067867, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19744878HCID 19744878, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Then, 21.03 g of the so-obtained 4,4'-dibenzyloxy-2'-hydroxy-3'-(3-methyl-2-butenyl)chalcone was added to 200 ml of an ethyl acetate suspension of 7.01 g of 5% palladium/carbon, in which hydrogen had been adsorbed in advance, and the mixture was stirred at room temperature for 6 hours and hydrogen was absorbed. After the reaction, the suspension was filtered to remove the palladium/carbon, and the solvent was removed from the filtrate by distillation and the obtained residue was recrystallized from benzene to obtain 11.85 g (yield=86.6%) of 1-(2,4-dihydroxy-3-isopentylphenyl)-3-(4-hydroxyphenyl)-1-propanone in the form of a colorless needle.

Workup

  1. customhydrogen was absorbed
  2. customAfter the reaction
  3. filtrationthe suspension was filtered
  4. customto remove the palladium/carbon
  5. customthe solvent was removed from the filtrate by distillation
  6. customthe obtained residue was recrystallized from benzene

Sources & evidence

ORD record
ord-50a7f9db7ee64183a5ae53d5c89e213d
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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