Water → Flavokavain A

HRID 364656

Reaction equation

HRID 364656 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[C:12](=[O:14])[CH3:13].[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]=O)=[CH:21][CH:22]=1.[OH-].[K+].O>C(O)C>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[C:12](=[O:14])[CH:13]=[CH:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH3:15])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 312444-MethoxybenzaldehydeHCID 66654Xanthoxylin

Product 1

HCID 235736Flavokavain AYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution containing 196 mg of 2'-hydroxy-4',6'-dimethoxyacetophenone and 150 mg of anisaldehyde in 3 ml of ethanol was added 50% aqueous potassium hydroxide (3 ml). After being stirred at room temperature for 3 days, the mixture was poured into 30 ml of cold water. The mixture was then extracted with three 30 ml portions of ethyl acetate. The combined ethyl acetate extracts were washed with water, dried over anhydrous sodium sulfate and then evaporated under reduced pressure to give a crystalline residue. Recrystallization of the residue from methanol gave 182 mg (50% yield) of 2'-hydroxy-4,4',6'-trimethoxychalcone as yellow needles: m.p. 110.7° C.

Workup

  1. extractionThe mixture was then extracted with three 30 ml portions of ethyl acetate
  2. washThe combined ethyl acetate extracts were washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customto give a crystalline residue
  6. customRecrystallization of the residue from methanol

Sources & evidence

ORD record
ord-7b4b85d9d4c8416dbac5f909abb7e2ae
Source dataset
uspto-grants-1986_08
Patent number
US04605674

Linked notes

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