HCID 53742999, compound → HCID 14368075, compound

HRID 1030718Notes

Reaction equation

HRID 1030718 reaction equation
[OH:1][C:2]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:3]=1[C:4](=[O:21])[CH:5]=[CH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH2:16][O:17][CH3:18])=[C:9]([O:19][CH3:20])[CH:8]=1.[H][H]>[Pd].C(OCC)(=O)C>[OH:1][C:2]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:3]=1[C:4](=[O:21])[CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH2:16][O:17][CH3:18])=[C:9]([O:19][CH3:20])[CH:8]=1

Participants

5

Reactant 2

HCID 53742999HCID 53742999, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 14368075HCID 14368075, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

An ethyl acetate solution of 2.8 g of the so-obtained 2'-hydroxy-3,5,4',6'-tetramethoxy-4-methoxymethoxy-3'-(3-methyl-2-butenyl)chalcone was added to 20 ml of an ethyl acetate solution of 0.4 g of palladium/carbon, in which hydrogen had been adsorbed in advance, and hydrogen was further adsorbed with strong stirring. Then, the mixture was stirred overnight, the palladium/carbon was removed by using Celite, and the residue was dissolved in ether and crystallized from hexane to obtain 2.6 g (yield=94%) of 1-(2-hydroxy-4,6-dimethoxy-3-isopentylphenyl)-3-(3,5-dimethoxy-4-methoxymethoxyphenyl)-1-propanone in the form of a white solid.

Workup

  1. customthe palladium/carbon was removed
  2. dissolutionthe residue was dissolved in ether
  3. customcrystallized from hexane

Sources & evidence

ORD record
ord-ec9c6615511b4320858f4beb451a5de3
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

Loading…