Hydrochloric Acid → 4-Oxocyclohexane-1-carbonitrile

HRID 491897Notes

Reaction equation

HRID 491897 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]#[N:12])[CH2:7][CH2:6]2)[O:4]CC1.Cl>CC(C)=O>[O:4]=[C:5]1[CH2:10][CH2:9][CH:8]([C:11]#[N:12])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 111164331,4-Dioxaspiro[4.5]decane-8-carbonitrile

Product 1

HCID 122356394-Oxocyclohexane-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. temperaturewas refluxed overnight
  2. customThe acetone was removed by evaporation
  3. extractionThe aqueous phase was extracted with ethyl acetate three times
  4. washThe combined organic extracts were washed with water one time
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe solution was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-099d10338d1e4bf1b1417a70d6651eb2
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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