p-Toluenesulfonic acid → HCID 10977233, Verbindung

HRID 321908

Reaktionsgleichung

Reaktionsgleichung von HRID 321908
[C@H:1]12[C:10](=O)[O:9][C:7](=[O:8])[C@H:3]([CH2:4][CH2:5][CH2:6]1)[CH2:2]2.[CH:12]([O:19]CC)([O:16][CH2:17][CH3:18])OCC.[C:22]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[C@H:5]1([C:12]([O:16][CH2:17][CH3:18])=[O:19])[CH2:6][CH2:1][CH2:2][C@@H:3]([C:7]([O:9][CH2:10][CH3:22])=[O:8])[CH2:4]1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 11367118cis-1,3-Cyclohexanedicarboxylic anhydride

Produkt 1

HCID 10977233HCID 10977233, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Anhydride 1 (7.71 g; 50 mmol) was combined with triethyl orthoformate (12.5 mL; 75 mmol; 1.5 equiv) and ethanol (50 mL). p-Toluenesulfonic acid (0.48 g; 2.5 mmol; 0.05 equiv) was added and the reaction mixture was heated overnight at 60° C. to completely consume 1. Solid sodium bicarbonate (0.5 g) was added and the solvent was removed at reduced pressure. The residue was dissolved in toluene (25 mL), washed with saturated aqueous NaHCO3 (5 mL), dried over Na2SO4, and concentrated to afford 11.42 g (99%) of cis-2b which was a single peak by GC analysis.

Aufarbeitung

  1. customto completely consume 1
  2. additionSolid sodium bicarbonate (0.5 g) was added
  3. customthe solvent was removed at reduced pressure
  4. dissolutionThe residue was dissolved in toluene (25 mL)
  5. washwashed with saturated aqueous NaHCO3 (5 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto afford 11.42 g (99%) of cis-2b which

Quellen und Nachweise

ORD-Eintrag
ord-103a8571befd42b9b33d9e2537247ea4
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06210956B1

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