HCID 22269477, compound → HCID 22269470, compound

HRID 983735Notes

Reaction equation

HRID 983735 reaction equation
[CH:1]([C:5]1[CH:36]=[CH:35][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]([CH:30]([CH2:32][CH3:33])[CH3:31])=[CH:26][CH:25]=3)=[CH:16][C:12]=2[C:13]([OH:15])=[O:14])=O)=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2].[H][H]>[Pd].O1CCCC1>[CH: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:35]=[CH:36][C:5]([CH:1]([CH2:3][CH3:4])[CH3:2])=[CH:6][CH:7]=3)=[CH:19][C:18]=2[C:20]([OH:22])=[O:21])=[CH:25][CH:26]=1)([CH2:32][CH3:33])[CH3:31]

Participants

5

Reactant 2

HCID 22269477HCID 22269477, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22269470HCID 22269470, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 120 grams of 2,5-bis(4-sec-butylbenzoyl)terephthalic acid, 1.5 L of tetrahydrofuran, and 9.65 grams of 10% palladium on carbon (as a catalyst) was heated at 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 solid. The solid was triturated with 10% ethyl acetate in heptane, collected and dried to give 2,5-bis(4-sec-butylbenzyl)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 10% ethyl acetate in heptane
  7. customcollected
  8. customdried

Sources & evidence

ORD record
ord-fa813a20fd064bd08a4d0e5e50dfd180
Source dataset
uspto-grants-2005_03
Patent number
US06864396B2

Reaction notes

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