반응 #409090

반응 방정식

Anhydride

cis-1,3-Cyclohexanedicarboxylic Anhydride

triethyl orthoformate

p-Toluenesulfonic acid

→

Diethyl cis-1,3-Cyclohexanedicarboxylate

용매

ethanol

반응 조건

후처리

1. 1
   기타to completely consume 1
2. 2
   workup.ADDITIONSolid sodium bicarbonate (0.5 g) was added
3. 3
   기타the solvent was removed at reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in toluene (25 mL)
5. 5
   세척washed with saturated aqueous NaHCO3 (5 mL)
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated
8. 8
   기타to afford 11.42 g (99%) of cis-2b which

실험 절차

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.

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