p-Toluenesulfonic acid → Dimethyl cis-1,3-cyclohexanedicarboxylate

HRID 321907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 321907
[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:17]C)([O:15][CH3:16])OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C@H:1]1([C:12]([O:15][CH3:16])=[O:17])[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 11367118cis-1,3-Cyclohexanedicarboxylic anhydride

Produkt 1

HCID 11264108Dimethyl cis-1,3-cyclohexanedicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Anhydride 1 (3.85 g; 25 mmol) was combined with trimethyl orthoformate (4.10 mL; 37.5 mmol; 1.5 equiv) and methanol (8.2 mL). p-Toluenesulfonic acid (238 mg; 1.25 mmol; 0.05 equiv) was added and the reaction mixture was stirred overnight at ambient temperature to completely consume 1 and afford a single product by GC analysis. The solvent was removed at reduced pressure and the residue was dissolved in ethyl acetate (30 mL), washed with saturated aqueous NaHCO3 (10 mL), dried over MgSO4, and concentrated to afford 4.91 g (98%) of cis-2a which gave a single peak by GC analysis.

Aufarbeitung

  1. customto completely consume 1
  2. customafford a single product by GC analysis
  3. customThe solvent was removed at reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate (30 mL)
  5. washwashed with saturated aqueous NaHCO3 (10 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto afford 4.91 g (98%) of cis-2a which
  9. customgave a single peak by GC analysis

Quellen und Nachweise

ORD-Eintrag
ord-c1f93ca583934ed2818a6bcce288eb16
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06210956B1

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