Water → Daidzein diacetate

HRID 603265Notes

Reaction equation

HRID 603265 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].N1[CH:32]=[CH:31]C=CC=1.[OH2:33]>>[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:31]([CH3:32])=[O:33])=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:1][CH:2]=1)=[O:22]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 5281708Daidzein

Product 1

HCID 10359753Daidzein diacetateYield 83%

Procedure

A mixture of daidzein (1.0 g, 3.9 mmol), acetic anhydride (5 ml) and pyridine (5 ml) was left in the dark at room temperature for 24 h. The reaction mixture was poured into water (100 ml), stirred for 2 h and then extracted with dichloromethane (3×50 ml). The dichloromethane layer was washed with water, dried over anhydrous sodium sulfate and evaporated. The white residue was crystallised from methanol to yield daidzein diacetate as white prisms (1.1 g, 83%). 1H NMR (CDCl3): δ 2.32 (s, 3H, OCOCH3), 2.36 (s, 3H, OCOCH3), 7.18 (d, 2H, J 9.2 Hz, ArH), 7.19 (d, 1H, J 9.0 Hz, H6), 7.31 (d, 1H, J 2.0 Hz H8), 7.59 (d, 2H, J 9.2 Hz, ArH), 8.00 (s, 1H, H2), 8.33 (d, 2H, J 8.2 Hz, ArH).

Workup

  1. extractionextracted with dichloromethane (3×50 ml)
  2. washThe dichloromethane layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe white residue was crystallised from methanol

Sources & evidence

ORD record
ord-e487187fc73b4ec0b3464b1a35b8712d
Source dataset
uspto-grants-2011_03
Patent number
US07906660B2

Reaction notes

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