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

HRID 983731Notes

Reaction equation

HRID 983731 reaction equation
[CH2:1]([C:13]1[CH:52]=[CH:51][C:16]([C:17]([C:19]2[CH:27]=[C:26]([C:28]([OH:30])=[O:29])[C:25]([C:31](=O)[C:32]3[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])=[CH:34][CH:33]=3)=[CH:24][C:20]=2[C:21]([OH:23])=[O:22])=O)=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H][H]>[Pd].O1CCCC1>[CH2:38]([C:35]1[CH:36]=[CH:37][C:32]([CH2:31][C:25]2[CH:24]=[C:20]([C:21]([OH:23])=[O:22])[C:19]([CH2:17][C:16]3[CH:15]=[CH:14][C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:52][CH:51]=3)=[CH:27][C:26]=2[C:28]([OH:30])=[O:29])=[CH:33][CH:34]=1)[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Participants

5

Reactant 2

HCID 222694792,5-Bis(4-dodecylbenzoyl)terephthalic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 222694382,5-Bis(4-dodecylbenzyl)terephthalic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 133 grams of 2,5-bis(4-dodecylbenzoyl)terephthalic acid and 1 L of tetrahydrofuran was treated with 8 grams of 10% palladium on carbon (as a catalyst) and heated to 65° C. for 17 hours in an atmosphere of hydrogen at 270 kPa. The reaction mixture was filtered through Celite™ diatomaceous earth filter agent to remove the catalyst. The filtrate was concentrated in vacuo to give a white solid. The solid was triturated with ethyl acetate, and the residue was dried to give 2,5-bis(4-dodecylbenzyl)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 white solid
  6. customThe solid was triturated with ethyl acetate
  7. customthe residue was dried

Sources & evidence

ORD record
ord-7204e3caee724ad0a461fc256c9d562a
Source dataset
uspto-grants-2005_03
Patent number
US06864396B2

Reaction notes

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