2,5-bis(4-methylbenzoyl)terephthalic Acid → 2,5-Bis(4-methylbenzyl)terephthalic acid

HRID 488948Notes

Reaction equation

HRID 488948 reaction equation
[CH3:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([C:8]2[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[C:14]([C:20](=O)[C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=O)=[CH:4][CH:3]=1.[H][H]>[Pd].C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:8]2[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[C:14]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=3)=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 112581482,5-bis(4-methylbenzoyl)terephthalic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 117491572,5-Bis(4-methylbenzyl)terephthalic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 30.0 grams of 2,5-bis(4-methylbenzoyl)terephthalic acid, 500 mL of acetic acid, and 3 grams of 5% palladium on activated carbon (as a catalyst) was heated to 64° C. for 17 hours in an atmosphere of hydrogen at 270 kPa. The mixture was filtered to remove the catalyst and the product. The catalyst and the product were slurried in 500 mL of tetrahhydrofuran and filtered through Celite™ diatomaceous earth filter agent. The resulting filtrate was concentrated in vacuo. The resulting wet solid was slurried in ethyl acetate and collected by filtration and dried to give 2,5-bis(4-methylbenzyl)terephthalic acid.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. filtrationfiltered through Celite™ diatomaceous earth
  4. filtrationfilter agent
  5. concentrationThe resulting filtrate was concentrated in vacuo
  6. filtrationcollected by filtration
  7. customdried

Sources & evidence

ORD record
ord-6d8fde46ea5f4333aa8ec5532b4ba027
Source dataset
uspto-grants-2005_12
Patent number
US06974877B2

Reaction notes

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