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

HRID 1190072Notes

Reaction equation

HRID 1190072 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.[OH-].[Na+]>C1COCC1.Cl>[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 14798Sodium HydroxideHCID 187284658-Methyl-1,4-dioxaspiro[4.5]decane-8-carbonitrile

Product 1

HCID 142273931-Methyl-4-oxocyclohexane-1-carbonitrileYield 73.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

8-methyl-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (3.29 g, 18.1 mmol) was dissolved in a 1:1 mixture of THF and 3N HCl aqueous solution (60 mL). The resulting mixture was stirred at 40° C. for 5 h, cooled to 0° C. and neutralized using about 30 mL of a 3N NaOH aqueous solution until a basic pH was reached. It was extracted with ether (4×75 mL). The organic portions were combined, dried over anhydrous Na2SO4 and concentrated. The crude was purified by silica gel column chromatography using a gradient from 15% EtOAc:hexanes to 20% EtOAc:hexanes as eluent to afford 1-Methyl-4-oxo-cyclohexanecarbonitrile as a white solid (1.82 g, 73%).

Workup

  1. temperaturecooled to 0° C.
  2. extractionIt was extracted with ether (4×75 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-548800010b04460ab0814707e9644d2a
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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