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

HRID 983725
Notes
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Reaction equation

HRID 983725 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:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(N([CH:39]([CH3:41])[CH3:40])CC)(C)C.Cl>ClCCCl.O>[CH2:21]([C:27]1[CH:28]=[CH:29][C:30]([C:19]([C:6]2[CH:5]=[C:10]([C:11]([OH:13])=[O:12])[C:9]([C:14](=[O:15])[C:30]3[CH:31]=[CH:32][C:27]([CH2:21][CH2:22][CH2:23][CH2:41][CH2:39][CH3:40])=[CH:28][CH:29]=3)=[CH:8][C:7]=2[C:16]([OH:18])=[O:17])=[O:20])=[CH:31][CH:32]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6966Pyromellitic dianhydrideHCID 14109HexylbenzeneHCID 81531DiisopropylethylamineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 222694532,5-Bis(4-hexylbenzoyl)terephthalic acid

Reagents, catalysts & solvents

2
HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

To a mixture of 25.7 grams of aluminum chloride, 51.3 mL of 1,2-dichloroethane, and 10 grams of benzene-1,2,4,5-tetracarboxylic acid dianhydride (pyromellitic dianhydride) was added with cooling, a solution of 14.9 grams of hexylbenzene and 6.40 grams of diisopropylethylamine in 25 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 for an additional 15 minutes after the addition was complete, and it was then heated to 40° C. for one hour. The warm mixture was poured into a beaker with 200 grams of ice and 75 mL of concentrated hydrochloric acid and stirred overnight at room temperature. The aqueous phase was poured off and the resulting oily solid was stirred with 500 mL of water, and the water was poured off. This water wash was repeated, and the resulting residue was dissolved in 250 mL of acetone and concentrated in vacuo. This residue was stirred with 55 mL of ethyl acetate, and the resulting solid was collected by filtration, washed with 100 mL of ethyl acetate, and dried to give 2,5-bis(4-hexylbenzoyl)terephthalic acid.

Workup

  1. additionwas added
  2. temperaturewith cooling
  3. customthe temperature between 15° C. and 20° C
  4. additionafter the addition
  5. stirringstirred overnight at room temperature
  6. additionThe aqueous phase was poured off
  7. washThis water wash
  8. dissolutionthe resulting residue was dissolved in 250 mL of acetone
  9. concentrationconcentrated in vacuo
  10. stirringThis residue was stirred with 55 mL of ethyl acetate
  11. filtrationthe resulting solid was collected by filtration
  12. washwashed with 100 mL of ethyl acetate
  13. customdried

Sources & evidence

ORD record
ord-f5f81bd6fa234b2d8d8e6716c744838b
Source dataset
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06864396B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes