Hydrochloric Acid → HCID 12644485, compound

HRID 1885652Notes

Reaction equation

HRID 1885652 reaction equation
[O:1]([C:8]1[CH:36]=[CH:35][C:11]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:34])[C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:41](Cl)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.Cl.[OH-:51].[Na+]>ClC1C=CC=CC=1Cl>[C:41]([C:5]1[CH:4]=[CH:3][C:2]([O:1][C:8]2[CH:36]=[CH:35][C:11]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:34])[C:21]4[CH:26]=[CH:25][C:24]([O:27][C:28]5[CH:29]=[CH:30][C:31]([C:12](=[O:51])[C:11]6[CH:35]=[CH:36][CH:8]=[CH:9][CH:10]=6)=[CH:32][CH:33]=5)=[CH:23][CH:22]=4)=[CH:16][CH:15]=3)=[O:13])=[CH:10][CH:9]=2)=[CH:7][CH:6]=1)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7412Benzoyl chloride2×HCID 14798Sodium HydroxideHCID 2058710Methanone, 1,4-phenylenebis[(4-phenoxyphenyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 12644485HCID 12644485, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent2×

Procedure

In a 2 liter flask equipped with a nitrogen inlet, mechanical stirrer and condenser (with nitrogen outlet) were charged 100 g (0.2125 moles) of 1,4-bis (4-phenoxybenzoyl)benzene (DTD), 179 g (1.34 moles) of aluminum chloride and 800 ml of o-dichlorobenzene. To this stirring solution, 49.34 ml of benzoyl chloride (59.77 g, 0.4251 moles) in 200 ml o-dichlorobenzene were added dropwise at room temperature over 0.5 hr. The temperature rose somewhat during benzoyl chloride addition and after the addition was complete, the reaction temperature was raised to 95°-100° C. and held for about 2.5 hrs. Hydrochloric acid generated during the reaction was swept out with nitrogen and neutralized with aqueous sodium hydroxide solution. Afterwards, the reaction solution was cooled to room temperature and precipitated into methanol. The solid product was filtered off and allowed to air dry. It was then dissolved in hot o-dichlorobenzene, filtered through a heated coarse fritted filter, and allowed to cool and crystallize. After filtration, the white crystalline product was slurried twice in methanol to remove residual o-dichlorobenzene and then dried under vacuum with an nitrogen bleed at 150° C. A single, sharp melting point (by DSC, 20° C./min) was found for this material at 287.5° C. (peak maximum).

Workup

  1. customIn a 2 liter flask equipped with a nitrogen inlet, mechanical stirrer and condenser (with nitrogen outlet)
  2. additionafter the addition
  3. temperaturethe reaction temperature was raised to 95°-100° C.
  4. customprecipitated into methanol
  5. filtrationThe solid product was filtered off
  6. customto air dry
  7. dissolutionIt was then dissolved in hot o-dichlorobenzene
  8. filtrationfiltered through
  9. temperaturea heated coarse fritted filter
  10. temperatureto cool
  11. customcrystallize
  12. filtrationAfter filtration
  13. customto remove residual o-dichlorobenzene
  14. customdried under vacuum with an nitrogen
  15. custombleed at 150° C
  16. customwas found for this material at 287.5° C.

Sources & evidence

ORD record
ord-4941e3365cf24d8d8f40e9b3f519a233
Source dataset
uspto-grants-1992_09
Patent number
US05145899

Reaction notes

Loading…