Hydrochloric Acid → 2,5-Bis(2,5-dimethybenzoyl)terephthalic acid

HRID 488965

Reaction equation

HRID 488965 reaction equation
[CH:1]1[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=2[CH:4]=[C:3]2[C:12]([O:14][C:15](=[O:16])[C:2]=12)=[O:13])=[O:8].[Cl-].[Al+3].[Cl-].[Cl-].C(N(CC)[CH:25]([CH3:27])[CH3:26])(C)C.Cl.[CH3:31][C:32]1[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=1>ClCCCl>[CH3:15][C:2]1[CH:3]=[CH:27][C:25]([CH3:26])=[CH:6][C:1]=1[C:15]([C:2]1[CH:1]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([C:10](=[O:11])[C:33]2[CH:34]=[C:35]([CH3:38])[CH:36]=[CH:37][C:32]=2[CH3:31])=[CH:4][C:3]=1[C:12]([OH:14])=[O:13])=[O:16]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6966Pyromellitic dianhydrideHCID 7809P-XyleneHCID 81531DiisopropylethylamineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 225613632,5-Bis(2,5-dimethybenzoyl)terephthalic acid

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
15 °C

Procedure

A mixture of 144 grams of benzene-1,2,4,5-tetracarboxylic acid dianhydride (pyromellitic dianhydride), 439 grams of aluminum chloride, and 915 grams of 1,2-dichloroethane was cooled to 15° C. To this was added a mixture of 140 grams of p-xylene, 109 grams of N,N-diisopropylethylamine, and 426 mL of 1,2-dichloroethane over a period of 3.5 hours keeping the temperature between 15° C. and 20° C. The resulting mixture was stirred overnight at room temperature, poured into 2876 grams of ice and 1078 mL concentrated hydrochloric acid and stirred for one hour. The organic layer was washed with 7 L of water. Three liters of water was poured off and the mixture allowed to stand for 4 days, after which the remaining 3 L of water was poured off. To the resulting residue was added 7 L of ethyl acetate and 3 L of tetrahydrofuran. The organic phase was separated and concentrated in vacuo. To 92 grams of the residue was added 1910 mL of ethyl acetate and the mixture was heated to 77° C. for one hour. The mixture was cooled to room temperature and the solid was collected by filtration and dried to give 2,5-bis(2,5-dimethybenzoyl)terephthalic acid.

Workup

  1. additionTo this was added
  2. customthe temperature between 15° C. and 20° C
  3. stirringstirred for one hour
  4. washThe organic layer was washed with 7 L of water
  5. additionThree liters of water was poured off
  6. waitto stand for 4 days
  7. additionafter which the remaining 3 L of water was poured off
  8. additionTo the resulting residue was added 7 L of ethyl acetate and 3 L of tetrahydrofuran
  9. customThe organic phase was separated
  10. concentrationconcentrated in vacuo
  11. additionTo 92 grams of the residue was added 1910 mL of ethyl acetate
  12. temperaturethe mixture was heated to 77° C. for one hour
  13. temperatureThe mixture was cooled to room temperature
  14. filtrationthe solid was collected by filtration
  15. customdried

Sources & evidence

ORD record
ord-1aa852da6f814d4ba199a95f4a4a6096
Source dataset
uspto-grants-2005_12
Patent number
US06974877B2

Linked notes

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