Water → Di-i-propyl cis-1,3-Cyclohexanedicarboxylate

HRID 377946

Reaktionsgleichung

Reaktionsgleichung von HRID 377946
[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.[CH:12]([OH:15])([CH3:14])[CH3:13].[C:16]1(C)[CH:21]=CC(S(O)(=O)=O)=C[CH:17]=1.O>C1(C)C=CC=CC=1>[C@H:3]1([C:7]([O:9][CH:16]([CH3:21])[CH3:17])=[O:8])[CH2:4][CH2:5][CH2:6][C@@H:1]([C:10]([O:15][CH:12]([CH3:14])[CH3:13])=[O:11])[CH2:2]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 3776IsopropanolHCID 6101p-Toluenesulfonic acidHCID 11367118cis-1,3-Cyclohexanedicarboxylic anhydride

Produkt 1

HCID 21967255Di-i-propyl cis-1,3-Cyclohexanedicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Anhydride 1 (1.21 g; 7.8 mmol) was dissolved in isopropanol (6.0 mL; 78 mmol; 10 equiv) and toluene (6 mL). p-Toluenesulfonic acid (74 mg; 0.39 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 7 hr at reflux, GC analysis indicated >96% conversion to 2d. The reaction mixture was washed with saturated aqueous sodium bicarbonate (2×10 mL). The organic solution was dried over MgSO4 and concentrated to afford cis-2d which was a single peak by GC analysis.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. distillationcould be continuously distilled
  3. temperatureAfter 7 hr at reflux
  4. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate (2×10 mL)
  5. dry with materialThe organic solution was dried over MgSO4
  6. concentrationconcentrated
  7. customto afford cis-2d which

Quellen und Nachweise

ORD-Eintrag
ord-126bed31673348488f4058f2a356eeff
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028213

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