Cyclohexane → 4-Pentylphenyl 4-hydroxybenzoate

HRID 1442482Notes

Reaction equation

HRID 1442482 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13](=[O:28])[C:14]2[CH:19]=[CH:18][C:17]([O:20]CC3C=CC=CC=3)=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C1CCCCC1>[OH-].[OH-].[Pd+2].C(O)C>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13](=[O:28])[C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 8078CyclohexaneHCID 138105764-Pentylphenyl 4-(benzyloxy)benzoate

Product 1

HCID 136605894-Pentylphenyl 4-hydroxybenzoateYield 93.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

15.6 g (41.5 mmol) of 4-benzyloxy-benzoic acid 4-pentyl-phenyl ester, 25 mL of cyclohexane and 0.78 g of palladium hydroxide/carbon were added to 100 mL of dehydrated ethanol and refluxed for 10 hours in the presence of argon. The resulting reaction mixture was filtered and the filtrate was concentrated. The residue was recrystallized from toluene to obtain 11.0 g of a white solid.

Workup

  1. temperaturerefluxed for 10 hours in the presence of argon
  2. customThe resulting reaction mixture
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-08c9694f227d46b08ab6b22a4e10ae29
Source dataset
uspto-grants-2010_02
Patent number
US07658979B2

Reaction notes

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