Reaction #579079

Reaction equation

1,4-dioxaspiro[4,5]decane-8-carbonitrile

hydrochloric acid

→

4-oxo-cyclohexanecarbonitrile

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturewas refluxed overnight
2. 2
   OtherThe acetone was removed by evaporation
3. 3
   ExtractionThe aqueous phase was extracted with ethyl acetate three times
4. 4
   WashThe combined organic extracts were washed with water one time
5. 5
   Dryingdried over magnesium sulfate
6. 6
   FiltrationThe solution was filtered
7. 7
   Concentrationconcentrated

Procedure

A solution of 1,4-dioxaspiro[4,5]decane-8-carbonitrile (15.86 g, 94.8 mmol) (prepared according to the procedure in Lucija Peterlin-Masic, Andreja Jurca, Petra Marrinko, Anita Jancar and Danijel Kikelj, Tetrahedron 2002, 58, 1557-1563), in a mixture of aqueous hydrochloric acid (2 N, 60 mL) and acetone (100 mL) was refluxed overnight. The acetone was removed by evaporation. The aqueous phase was extracted with ethyl acetate three times. The combined organic extracts were washed with water one time and then dried over magnesium sulfate. The solution was filtered and concentrated to yield 4-oxo-cyclohexanecarbonitrile as a colorless oil, which was used in the next reaction without purification.

Source