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

HRID 1442484Notes

Reaction equation

HRID 1442484 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].C1CCCCC1>[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 8078CyclohexaneHCID 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

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

Workup

  1. temperaturerefluxed for 12 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 hexane/ethyl acetate

Sources & evidence

ORD record
ord-57d650f7e82945b4ad821784138393b3
Source dataset
uspto-grants-2010_02
Patent number
US07658979B2

Reaction notes

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