Hydrochloric Acid → HCID 68991032, compound

HRID 1822097Notes

Reaction equation

HRID 1822097 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH:12]1[C:17]2[C:18]([O:20][C:21](=[O:22])[C:16]=2[CH:15]=[C:14]2[C:23]([O:25][C:26](=[O:27])[C:13]=12)=[O:24])=[O:19].Cl>C(OCC)(=O)C.O>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:26]([C:13]2[CH:12]=[C:17]([C:18]([OH:20])=[O:19])[C:16]([C:21](=[O:22])[C:6]3[CH:11]=[CH:10][C:9]([Cl:1])=[CH:8][CH:7]=3)=[CH:15][C:14]=2[C:23]([OH:25])=[O:24])=[O:27])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6966Pyromellitic dianhydrideHCID 7964ChlorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 68991032HCID 68991032, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 497.6 grams (3.732 moles, 4.2 eq) of aluminum chloride, 2000 grams (17.77 moles, 20 eq) of chlorobenzene, and 193.8 grams (0.8885 moles, 1 eq) of benzene-1,2,4,5-tetracarboxylic acid dianhydride (pyromellitic dianhydride) was stirred and heat to 65° C. for 3 hrs. The mixture was cooled to room temperature while stirring overnight. This mixture was slowly added to a mixture of 1048 grams of 12M hydrochloric acid and stirred for one hour. Six liters of water was added and the organic layer was separated. The organic layer was washed with water until the water layer had a pH of greater than 1. To the organic layer was added 1429 mL of ethyl acetate, and 400 mL THF and the aqueous phase was separated and the organic phase was washed with 500 mL saturated NaCl and split. The organic phase was dried with magnesium sulfate and the solvent removed in vacuum to give 287.9 grams. This material was heated with three liters of ethyl acetate at 75° C. for five hours and then cooled. The solid was collected and air dried to give 95.73 grams of the desired product. 1H NMR (400 MHz, DMSO-d6): δ7.951 (s, 2H), 7.748 (d, J=8.60 Hz, 4H), 7.58 (d, J=8.60 Hz, 4H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringwhile stirring overnight
  3. stirringstirred for one hour
  4. customthe organic layer was separated
  5. washThe organic layer was washed with water until the water layer
  6. additionTo the organic layer was added 1429 mL of ethyl acetate, and 400 mL THF
  7. customthe aqueous phase was separated
  8. washthe organic phase was washed with 500 mL saturated NaCl
  9. customsplit
  10. dry with materialThe organic phase was dried with magnesium sulfate
  11. customthe solvent removed in vacuum
  12. customto give 287.9 grams
  13. temperaturecooled
  14. customThe solid was collected
  15. customair dried

Sources & evidence

ORD record
ord-6373e159023843b8befdbab1ae6baa53
Source dataset
uspto-grants-2009_10
Patent number
US07608679B2

Reaction notes

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