1-Butanol → Di-n-butyl cis-1,3-Cyclohexanedicarboxylate

HRID 321911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 321911
[C@H:1]12[C:10](=[O:11])[O:9][C:7](=[O:8])[C@H:3]([CH2:4][CH2:5][CH2:6]1)[CH2:2]2.[CH2:12](O)[CH2:13][CH2:14][CH3:15].[C:17]1(C)C=C[CH:20]=[CH:19][CH:18]=1.C1(C)C=CC(S(O)(=O)=[O:31])=CC=1>O>[C@H:3]1([C:7]([O:8][CH2:17][CH2:18][CH2:19][CH3:20])=[O:31])[CH2:4][CH2:5][CH2:6][C@@H:1]([C:10]([O:9][CH2:12][CH2:13][CH2:14][CH3:15])=[O:11])[CH2:2]1

Komponenten

6

Edukt 4

HCID 2631-ButanolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 11367118cis-1,3-Cyclohexanedicarboxylic anhydride

Produkt 1

HCID 21967256Di-n-butyl cis-1,3-Cyclohexanedicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Anhydride 1 (3.85 g; 25 mmol) was combined with n-butanol (11.4 mL; 125 mmol; 5 equiv) and toluene (25 mL). p-Toluenesulfonic acid (238 mg; 1.25 mmol; 0.05 equiv) was added and the reaction mixture was heated to reflux under conditions where water could be continuously distilled using a Dean-Stark trap. After 2.5 h at reflux, GC analysis indicated no residual 1. The reaction mixture was washed with saturated aqueous sodium bicarbonate (5 mL).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. distillationcould be continuously distilled
  3. temperatureAfter 2.5 h at reflux
  4. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate (5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-6af23158ba5b48f1a32a46fae7cb20ac
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06210956B1

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