Reaction #674305

Reaction equation

4-(benzyloxy)cyclohexanecarboxamide

trifluoroacetic anhydride

H2O

→

4-(benzyloxy)cyclohexanecarbonitrile

Yield 97.5%

Solvents

THF

Conditions

Workup

1. 1
   Concentrationconcentrated
2. 2
   Otherto give the residue
3. 3
   ExtractionThe aqueous phase was extracted with MTBE (3×50 mL)
4. 4
   WashThe combined organic solution was washed with brine (50 mL)
5. 5
   Dryingdried over anhydrous Na2SO4
6. 6
   Concentrationconcentrated

Procedure

To a suspension of 4-(benzyloxy)cyclohexanecarboxamide (2.33 g, 10 mmol, 1.0 equiv) in THF (dry, 50 mL) was added trifluoroacetic anhydride (4.16 mL, 30 mmol, 3.0 equiv) dropwise at room temperature. The resulting clear solution was stirred at room temperature for 30 min and then concentrated to give the residue. H2O (50 mL) was added. The aqueous phase was extracted with MTBE (3×50 mL). The combined organic solution was washed with brine (50 mL), dried over anhydrous Na2SO4, concentrated to give 2.1 g (yield 97%) of 4-(benzyloxy)cyclohexanecarbonitrile as a pale yellow oil.

Source