HCID 86745707, compound → HCID 14368072, compound

HRID 1030714Notes

Reaction equation

HRID 1030714 reaction equation
[H][H].[OH:3][C:4]1[C:25]([CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29])=[C:24]([O:31][CH3:32])[CH:23]=[C:22]([O:33][CH3:34])[C:5]=1[C:6](=[O:21])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][O:19][CH3:20])[CH:10]=1>[Pd].C(OCC)(=O)C>[OH:3][C:4]1[C:25]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[C:24]([O:31][CH3:32])[CH:23]=[C:22]([O:33][CH3:34])[C:5]=1[C:6](=[O:21])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][O:19][CH3:20])[CH:10]=1

Participants

5

Reactant 2

HCID 86745707HCID 86745707, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 14368072HCID 14368072, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To 40 ml of an ethyl acetate solution of 0.7 g of 5% palladium/carbon, in which hydrogen had been adsorbed in advance, was added 160 ml of an ethyl acetate solution of 5.0 g of the so-obtained 2'-hydroxy-4,4',6'-trimethoxy-3-methoxymethoxy-3'-(3-methyl-2-butenyl)chalcone, and hydrogen was further adsorbed with strong stirring. Then the mixture was stirred overnight, and the palladium/carbon was removed by using Celite and the solvent was removed by distillation. The residue was dissolved in diethyl ether and crystallized by addition of hexane to obtain 4.4 g (yield=91%) of 1-(2-hydroxy-4,6-dimethoxy-3-isopentylphenyl)-3-(4-methoxy-3-methoxymethoxyphenyl)-1-propanone in the form of a white solid.

Workup

  1. customthe palladium/carbon was removed
  2. customthe solvent was removed by distillation
  3. dissolutionThe residue was dissolved in diethyl ether
  4. customcrystallized by addition of hexane

Sources & evidence

ORD record
ord-fc51d47338c843a2aaccb933d8a4caca
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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