Reacción #409089

Ecuación de reacción

Anhydride

cis-1,3-Cyclohexanedicarboxylic Anhydride

trimethyl orthoformate

p-Toluenesulfonic acid

→

Dimethyl cis-1,3-Cyclohexanedicarboxylate

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto completely consume 1
2. 2
   Otroafford a single product by GC analysis
3. 3
   OtroThe solvent was removed at reduced pressure
4. 4
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate (30 mL)
5. 5
   Lavadowashed with saturated aqueous NaHCO3 (10 mL)
6. 6
   Secadodried over MgSO4
7. 7
   Concentraciónconcentrated
8. 8
   Otroto afford 4.91 g (98%) of cis-2a which
9. 9
   Otrogave a single peak by GC analysis

Procedimiento

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.

Fuente