Cyclohexene → 2-Chloro-4-hydroxy-benzoic acid 4-(4-pentyl-phenoxycarbonyl)-phenyl ester

HRID 2356175Notes

Reaction equation

HRID 2356175 reaction equation
[CH2:1]([C:6]1[CH:38]=[CH:37][C:9]([O:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20](=[O:36])[C:21]3[CH:26]=[CH:25][C:24]([O:27]CC4C=CC=CC=4)=[CH:23][C:22]=3[Cl:35])=[CH:15][CH:14]=2)=[O:12])=[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:38]=[CH:37][C:9]([O:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20](=[O:36])[C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=3[Cl:35])=[CH:15][CH:14]=2)=[O:12])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 684206604-Benzyloxy-2-chloro-benzoic acid 4-(4-pentyl-phenoxycarbonyl)-phenyl ester

Product 1

HCID 684197962-Chloro-4-hydroxy-benzoic acid 4-(4-pentyl-phenoxycarbonyl)-phenyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To 25 mL of dehydrated ethanol, 2.5 g (4.7 mmol) of 4-benzyloxy-2-chloro-benzoic acid 4-(4-pentyl-phenoxycarbonyl)-phenyl ester, 20 mL of cyclohexene, and 0.13 g of palladium hydroxide/carbon were added. Then, the mixture was refluxed for 12 hours under argon. The resulting reaction mixture was filtered, and the filtered liquid was concentrated. The residue was recrystallized from hexane/ethyl acetate. As a result, 1.65 g of a white solid was obtained.

Workup

  1. temperatureThen, the mixture was refluxed for 12 hours under argon
  2. customThe resulting reaction mixture
  3. filtrationwas filtered
  4. concentrationthe filtered liquid was concentrated
  5. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-7f2d476f0a234b9cbb73f326825b5899
Source dataset
uspto-grants-2010_07
Patent number
US07758932B2

Reaction notes

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