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

HRID 2356175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2356175
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7f2d476f0a234b9cbb73f326825b5899
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07758932B2

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