Sodium Bicarbonate → 1-Methyl-4-oxocyclohexane-1-carbonitrile

HRID 1948140Notes

Reaction equation

HRID 1948140 reaction equation
[CH3:1][C:2]1([C:12]#[N:13])[CH2:11][CH2:10][C:5]2(OCC[O:6]2)[CH2:4][CH2:3]1.C(=O)(O)[O-].[Na+]>C(O)(=O)C.[Cl-].[Na+].O>[CH3:1][C:2]1([C:12]#[N:13])[CH2:11][CH2:10][C:5](=[O:6])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 187284658-Methyl-1,4-dioxaspiro[4.5]decane-8-carbonitrile

Product 1

HCID 142273931-Methyl-4-oxocyclohexane-1-carbonitrileYield 62.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Alternatively the compound could be obtained by heating 14.2 g of 8-methyl-1,4-dioxa-spiro[4.5]decane-8-carbonitrile in 190 mL of 80% acetic acid under reflux until conversion was complete. The mixture was cooled and poured onto 1.2 L of cold, saturated sodium bicarbonate solution. 600 mL of brine were added and the mixture was extracted several times with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried over magnesium sulphate and evaporated. The residue was taken up in water and acetonitrile and lyophilized to give 6.75 g of the desired product, that could be directly used in further conversions.

Workup

  1. customAlternatively the compound could be obtained
  2. temperatureunder reflux until conversion
  3. temperatureThe mixture was cooled
  4. extractionthe mixture was extracted several times with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-4c9c90a15bbb41f4ba91c1a3a2013729
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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