Hydrochloric Acid → 2,5-Bis(4-dodecylbenzoyl)terephthalic acid

HRID 983730Notes

Reaction equation

HRID 983730 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1[C:10]2[C:11]([O:13][C:14](=[O:15])[C:9]=2[CH:8]=[C:7]2[C:16]([O:18][C:19](=[O:20])[C:6]=12)=[O:17])=[O:12].[CH2:21]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C(N([CH:45]([CH3:47])[CH3:46])CC)(C)C.Cl>O.C(OCC)(=O)C.O1CCCC1.ClCCCl>[CH2:21]([C:33]1[CH:34]=[CH:35][C:36]([C:19]([C:6]2[CH:5]=[C:10]([C:11]([OH:13])=[O:12])[C:9]([C:14](=[O:15])[C:36]3[CH:35]=[CH:34][C:33]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:47][CH2:45][CH3:46])=[CH:38][CH:37]=3)=[CH:8][C:7]=2[C:16]([OH:18])=[O:17])=[O:20])=[CH:37][CH:38]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 6966Pyromellitic dianhydrideHCID 31237DodecylbenzeneHCID 81531DiisopropylethylamineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 222694792,5-Bis(4-dodecylbenzoyl)terephthalic acid

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
16 °C

Procedure

To a mixture of 492 grams of aluminum chloride and 988 mL of 1,2-dichloroethane was added 192 grams of benzene-1,2,4,5-tetracarboxylic acid dianhydride (pyromellitic dianhydride). The resulting mixture was cooled to 16° C. and a solution of 434 grams of 1-dodecylbenzene, 123 grams of diisopropylethylamine and 480 mL of 1,2-dichloroethane was added over a period of 3.5 hours, keeping the temperature between 15° C. and 20° C. during the addition. The mixture was stirred overnight at room temperature and poured into a beaker of 1000 grams of ice and 1000 grams concentrated hydrochloric acid. The mixture was stirred for one hour and the liquid was poured from the coagulate. The mixture was divided into 800 mL portions and each portion was worked up as follows. To 800 mL of the mixture was added 800 mL of tetrahydrofuran, 800 mL of ethyl acetate, and 800 mL of water. The mixture was stirred and phase split. The organic phase was filtered and the filtrate was concentrated in vacuo. The residues were combined. To 127 grams of the combined residue was added 800 mL of ethyl acetate and the mixture was stirred until a suspension of a fine solid resulted. The solid was collected by filtration and washed with 50 mL of ethyl acetate. The solid was dried to give 2,5-bis(4-dodecylbenzoyl)terephthalic acid.

Workup

  1. customthe temperature between 15° C. and 20° C.
  2. additionduring the addition
  3. stirringThe mixture was stirred for one hour
  4. additionthe liquid was poured from the coagulate
  5. stirringThe mixture was stirred
  6. customphase split
  7. filtrationThe organic phase was filtered
  8. concentrationthe filtrate was concentrated in vacuo
  9. additionTo 127 grams of the combined residue was added 800 mL of ethyl acetate
  10. stirringthe mixture was stirred until a suspension of a fine solid
  11. customresulted
  12. filtrationThe solid was collected by filtration
  13. washwashed with 50 mL of ethyl acetate
  14. customThe solid was dried

Sources & evidence

ORD record
ord-791127531d9e4e238222cb898ebf9566
Source dataset
uspto-grants-2005_03
Patent number
US06864396B2

Reaction notes

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