Acetoacetic Acid → Daidzein diacetate

HRID 603266Notes

Reaction equation

HRID 603266 reaction equation
[CH:1]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[CH:14]=[CH:13][C:12]([OH:18])=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:5][CH:4]=[C:3]([OH:19])[CH:2]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21].[CH3:27][C:28](CC(O)=O)=[O:29]>N1C=CC=CC=1>[CH3:21][C:20]([O:19][C:3]1[CH:4]=[CH:5][C:6]([C:7]2[C:16](=[O:17])[C:15]3[CH:14]=[CH:13][C:12]([O:18][C:28]([CH3:27])=[O:29])=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:1][CH:2]=1)=[O:22]

Participants

5

Reactant 3

HCID 96Acetoacetic AcidHCID 7918Acetic AnhydrideHCID 5281708Daidzein

Product 1

HCID 10359753Daidzein diacetateYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of daidzein (2.0 g, 7.9 mmol), acetic anhydride (10 ml) and pyridine (2 ml) was heated on an oil bath at 105-110 C. for 1 h. After cooling the mixture to room temperature, it was stirred for a further 30 min during which time the diacetate crystallised from the solution. The product was filtered, washed thoroughly with water and recrystallised from methanol to yield daidzein diacetate as colourless prisms (2.4 g, 90%).

Workup

  1. temperaturewas heated on an oil bath at 105-110 C
  2. customcrystallised from the solution
  3. filtrationThe product was filtered
  4. washwashed thoroughly with water
  5. customrecrystallised from methanol

Sources & evidence

ORD record
ord-ab0565ea198d47e4a0528a2bc6b8b4fa
Source dataset
uspto-grants-2011_03
Patent number
US07906660B2

Reaction notes

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