Hydrochloric Acid → HCID 19744896, compound

HRID 2254246Notes

Reaction equation

HRID 2254246 reaction equation
[OH:1][C:2]1[C:19]([CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[C:18]([O:25][CH3:26])[CH:17]=[C:16]([O:27][CH3:28])[C:3]=1[C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[OH-].[K+].[H][H].Cl>C(OCC)(=O)C.[Pd].C(O)C>[CH3:26][O:25][C:18]1[CH:17]=[C:16]([O:27][CH3:28])[C:3]([C:4](=[O:15])[CH2:5][CH2:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[C:2]([OH:1])[C:19]=1[CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 4275190HCID 4275190, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19744896HCID 19744896, compoundYield 94.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Then, a liquid mixture of 16.2 g of 2'-hydroxy-4,4',6'-trimethoxy-3'-(3-methyl-2-butenyl)chalcone, 4.0 g of potassium hydroxide and 180 ml of ethanol was added to a suspension of 1.5 g of 5% palladium/carbon in 20 ml of ethyl acetate, in which a hydrogen gas had been sufficiently absorbed in advance, and the mixture was stirred at room temperature in a hydrogen gas atmosphere for 5 hours. After the reaction, the reaction mixture was made acidic by dilute hydrochloric acid, filtered, extracted with ethyl acetate and filtered, and the solvent was removed from the filtrate by distillation. The obtained residue was recrystallized from methanol to obtain 15.4 g (yield=94.6%) of 1-[4,6-dimethoxy-2-hydroxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-methoxyphenyl)-1-propanone in the form of a colorless needle.

Workup

  1. customhad been sufficiently absorbed in advance
  2. customAfter the reaction
  3. filtrationfiltered
  4. extractionextracted with ethyl acetate
  5. filtrationfiltered
  6. customthe solvent was removed from the filtrate by distillation
  7. customThe obtained residue was recrystallized from methanol

Sources & evidence

ORD record
ord-c8aa28c0e0f54f49942355223bd30035
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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