Iodine → 5,6,7,4'-Tetramethoxyflavone

HRID 1095269Notes

Reaction equation

HRID 1095269 reaction equation
[OH:1][C:2]1[C:7]([C:8](=[O:19])[CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[C:6]([O:20][CH3:21])[C:5]([O:22][CH3:23])=[C:4]([O:24][CH3:25])[CH:3]=1.II>CS(C)=O>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2[O:1][C:2]3[C:7]([C:8](=[O:19])[CH:9]=2)=[C:6]([O:20][CH3:21])[C:5]([O:22][CH3:23])=[C:4]([O:24][CH3:25])[CH:3]=3)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 807IodineHCID 3213486-hydroxy-1-(4-methoxycinnamoyl)-2,3,4-Trimethoxy-benzene

Product 1

HCID 961185,6,7,4'-TetramethoxyflavoneYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of the chalcone 6 (1.72 g, 5 mmol) and iodine (catalytic amount) in dimethyl sulfoxide (6 mL) was refluxed for 30 min, and then the reaction mixture was poured onto crushed ice (50 g). The resulting precipitate was collected and washed with 5% sodium thiosulfate solution (30 mL) and water. Recrystallization from ethanol afforded the title flavone (1.38 g, 81%) as bright yellow crystals: 1H NMR (CDCl3, 200 M Hz) δ 7.81 (d, J=9.0 Hz, 2H), 6.98 (d, J=9.0 Hz, 2H), 6.79 (s 1H), 6.57 (s, 1H), 3.99 (s 3H), 3.98 (s, 3H), 3.92 (s, 3H), 3.87 (s, 3H); 13C NMR (CDCl3, 50 M Hz) δ 177.1 (s), 162.0 (s), 161.0 (s), 157.5 (s), 154.3 (s), 152.4 (s), 140.2 (s), 127.5 (d, 2C), 123.6 (s), 114.2 (d, 2C), 122.7 (s), 106.8 (d), 96.1 (d), 62.0 (q), 61.4 (q), 56.1 (q), 55.3 (q).

Workup

  1. additionthe reaction mixture was poured
  2. customThe resulting precipitate was collected
  3. washwashed with 5% sodium thiosulfate solution (30 mL) and water
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-116026054b9a4fea9074215c19625a7b
Source dataset
uspto-grants-2012_03
Patent number
US08138165B2

Reaction notes

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