HCID 22633821, compound → HCID 22633809, compound

HRID 2417141Notes

Reaction equation

HRID 2417141 reaction equation
[C:1]1([O:7][C:8]2[CH:9]=[C:10]([CH:21]=[C:22]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:23]=2)[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Br>[C:25]1([O:24][C:22]2[CH:21]=[C:10]([CH:9]=[C:8]([O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:23]=2)[C:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[O:12])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 1

HCID 22633821HCID 22633821, compound

Product 1

HCID 22633809HCID 22633809, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent4×

Procedure

14.90 g (0.038 mole) of 3,5-diphenyloxy-4′-methoxybenzophenone are dissolved under argon in a mixture of 60 ml of hydrobromic acid (48% in water) and 120 ml of hydrobromic acid (33% solution in acetic acid). The mixture is stirred for 4 hours under reflux. A further 100 ml of hydrobromic acid (330/solution in acetic acid) and 50 ml of hydrobromic acid (48% in water) are added to the reaction solution. The reaction mixture is stirred for a further 6 hours under reflux. The reaction mixture is then poured onto ice and extracted several times with diethyl ether. The organic phases are combined and extracted several times with NaOH solution (20%). The aqueous phases are combined and washed neutral with HCl solution. The neutralised aqueous phase is then extracted several times with diethyl ether. The organic phases are combined, dried over magnesium sulfate, and the solvent is removed in vacuo. The crude product is taken up in a small amount of diethyl ether and filtered over silica gel. After removing the solvent and drying the residue in a high vacuum, 11.25 g (78%) of a white solid are obtained.

Workup

  1. temperatureunder reflux
  2. stirringThe reaction mixture is stirred for a further 6 hours
  3. temperatureunder reflux
  4. additionThe reaction mixture is then poured onto ice
  5. extractionextracted several times with diethyl ether
  6. extractionextracted several times with NaOH solution (20%)
  7. washwashed neutral with HCl solution
  8. extractionThe neutralised aqueous phase is then extracted several times with diethyl ether
  9. dry with materialdried over magnesium sulfate
  10. customthe solvent is removed in vacuo
  11. filtrationfiltered over silica gel
  12. customAfter removing the solvent
  13. dry with materialdrying the residue in a high vacuum, 11.25 g (78%) of a white solid
  14. customare obtained

Sources & evidence

ORD record
ord-f97f3191599641bba3249fe4db8ec5d5
Source dataset
uspto-grants-2004_11
Patent number
US06825312B2

Reaction notes

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