Cyclohexene → 4-Pentylphenyl 4-hydroxybenzoate

HRID 2356173Notes

Reaction equation

HRID 2356173 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].C1CCCCC=1>[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 8079CyclohexeneHCID 138105764-Pentylphenyl 4-(benzyloxy)benzoate

Product 1

HCID 136605894-Pentylphenyl 4-hydroxybenzoateYield 93.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To 100 mL of dehydrated ethanol, 15.6 g (41.5 mmol) of 4-benzyloxy-benzoic acid 4-pentyl-phenyl ester, 25 mL of cyclohexene, and 0.78 g of palladium hydroxide/carbon were added. Then, the mixture was refluxed for 10 hours under argon. The resulting reaction mixture was filtered, and the filtered liquid was concentrated. The residue was recrystallized from toluene. As a result, 11.0 g of a white solid was obtained.

Workup

  1. temperatureThen, the mixture was refluxed for 10 hours under argon
  2. customThe resulting reaction mixture
  3. filtrationwas filtered
  4. concentrationthe filtered liquid was concentrated
  5. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-cd5adff26bbe4a9fbbcacec78848cc75
Source dataset
uspto-grants-2010_07
Patent number
US07758932B2

Reaction notes

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