2,5-Bis(4-(3,5,5-trimethylhexyl)benzoyl)terephthalic acid → 2,5-Bis[4-(3,5,5-trimethylhexyl)benzyl]terephthalic acid

HRID 488972Notes

Reaction equation

HRID 488972 reaction equation
[CH3:1][CH:2]([CH2:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:3][CH2:4][C:5]1[CH:41]=[CH:40][C:8]([C:9]([C:11]2[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[C:17]([C:23](=O)[C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH:32]([CH3:38])[CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:26][CH:25]=3)=[CH:16][C:12]=2[C:13]([OH:15])=[O:14])=O)=[CH:7][CH:6]=1.[H][H]>O1CCCC1.[Pd]>[CH3:38][CH:32]([CH2:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH2:31][CH2:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][C:17]2[CH:16]=[C:12]([C:13]([OH:15])=[O:14])[C:11]([CH2:9][C:8]3[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][CH:2]([CH3:1])[CH2:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[CH:41][CH:40]=3)=[CH:19][C:18]=2[C:20]([OH:22])=[O:21])=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 222694372,5-Bis(4-(3,5,5-trimethylhexyl)benzoyl)terephthalic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 222694522,5-Bis[4-(3,5,5-trimethylhexyl)benzyl]terephthalic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture containing 20.0 grams of 2,5-bis[4-(3,5,5-trimethylhexyl)benzoyl]terephthalic acid in 1500 mL of tetrahydrofuran (THF) and 1.4 grams of 10% palladium on carbon (as a catalyst) was heated to 90° C. in an atmosphere of hydrogen at 620 kPa and 90° C. for 17 hours. The mixture was filtered through Celite™ diatomaceous earth filter agent to remove the catalyst. The filtrate was concentrated in vacuo to give 2,5-bis[4-(3,5,5-trimethylhexyl)benzyl]terephthalic acid.

Workup

  1. filtrationThe mixture was filtered through Celite™ diatomaceous earth
  2. filtrationfilter agent
  3. customto remove the catalyst
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9e592d40d35b4952a3076ab487712d7a
Source dataset
uspto-grants-2005_12
Patent number
US06974877B2

Reaction notes

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