Water → HCID 19804508, compound

HRID 1681984Notes

Reaction equation

HRID 1681984 reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:15](Cl)(=[O:25])[C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.[Cl-].[Al+3].[Cl-].[Cl-].[OH2:31]>ClC1C=CC=CC=1Cl>[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:15]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([C:4]2[CH:3]=[CH:2][C:1]3[O:31][C:11]4[C:12](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH2:13][C:14]=3[CH:5]=2)=[O:21])=[CH:18][CH:17]=1)=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 7107XantheneHCID 7488Terephthaloyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19804508HCID 19804508, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent2×

Procedure

1,4-Bis-(2-xanthenoyl)benzene was synthesized in this fashion: To a solution of 11.84 g of xanthene and 2.64 g of terephthaloyl chloride in 79 cc of o-dichlorobenzene chilled at 11° C. for 40 min,.was added, in a nitrogen atmosphere and without further cooling, 8.40 g of aluminum chloride portionwise so that the temperature did not rise above 26° C. The resulting deep reddish-brown solution was stirred for 45 min. It was then mixed with 240 cc of o-dichlorobenzene, and water was added. The mixture was heated to 98°-100° C. with stirring, and kept at that temperature for 30 min. Two layers formed. The organic layer was separated, and after cooling to room temperature, the solid that separated was collected by filtration. The solids were washed with methanol, methylene chloride, twice again with methanol, and dried under vacuum at ~90° C. for several hours. Mass spectrometry showed this solid to be the desired compound and indicated no impurities.

Workup

  1. customdid not rise above 26° C
  2. additionwas added
  3. temperatureThe mixture was heated to 98°-100° C.
  4. stirringwith stirring
  5. waitkept at that temperature for 30 min
  6. customTwo layers formed
  7. customThe organic layer was separated
  8. customthe solid that separated
  9. filtrationwas collected by filtration
  10. washThe solids were washed with methanol, methylene chloride, twice again with methanol
  11. customdried under vacuum at ~90° C. for several hours

Sources & evidence

ORD record
ord-1e29f47e7c7b4b9eb547be357a48c08d
Source dataset
uspto-grants-1992_12
Patent number
US05175218

Reaction notes

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