2,5-Bis(2,5-dimethybenzoyl)terephthalic acid → 2,5-Bis(2,5-dimethylbenzyl)terephthalic acid

HRID 488966Notes

Reaction equation

HRID 488966 reaction equation
[CH3:1][C:2]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:3]=1[C:4]([C:6]1[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[C:12]([C:18](=O)[C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=2[CH3:26])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])=O.[H][H]>O1CCCC1.[Pd]>[CH3:1][C:2]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:3]=1[CH2:4][C:6]1[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[C:12]([CH2:18][C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=2[CH3:26])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 225613632,5-Bis(2,5-dimethybenzoyl)terephthalic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 222694722,5-Bis(2,5-dimethylbenzyl)terephthalic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
117 °C

Procedure

A mixture of 92 grams of 2,5-bis(2,5-dimethybenzoyl)terephthalic acid in 1.5 L of tetrahydrofuran was treated with 9.2 grams of 10% palladium on carbon (as a catalyst) in an atmosphere of hydrogen at 270 kPa and 65° C. for 17 hours. The reaction mixture was filtered through Celite™ diatomaceous earth filter agent to remove the catalyst. The filtrate was concentrated in vacuo to give a solid. The solid was triturated with ethyl acetate, collected by filtration, and dried. To 75 grams of the solid was added 1250 grams of acetic acid, and the resulting mixture was heated to 117° C. for 30 minutes and cooled to room temperature. The resulting solid was collected by filtration and washed with acetic acid followed by heptane. The resulting residue was dried to give 2,5-bis(2,5-dimethybenzyl)terephthalic acid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite™ diatomaceous earth
  2. filtrationfilter agent
  3. customto remove the catalyst
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a solid
  6. customThe solid was triturated with ethyl acetate
  7. filtrationcollected by filtration
  8. customdried
  9. additionTo 75 grams of the solid was added 1250 grams of acetic acid
  10. temperaturecooled to room temperature
  11. filtrationThe resulting solid was collected by filtration
  12. washwashed with acetic acid
  13. customThe resulting residue was dried

Sources & evidence

ORD record
ord-27ca69c1d650401d86682b54153f6695
Source dataset
uspto-grants-2005_12
Patent number
US06974877B2

Reaction notes

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