Chloroacetonitrile → 1-Oxaspiro[2.5]octane-2-carbonitrile

HRID 1638770Notes

Reaction equation

HRID 1638770 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl[CH2:11][C:12]#[N:13]>ClCCl>[O:7]1[C:1]2([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:11]1[C:12]#[N:13]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 7967CyclohexanoneHCID 14798Sodium Hydroxide

Product 1

HCID 5489391-Oxaspiro[2.5]octane-2-carbonitrileYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of cyclohexanone (5.39 g, 0.055 mol), 50% sodium hydroxide solution (10 ml) and compound 1 (1 mmol) was added dropwise chloroacetonitrile (3.8 g, 0.05 mol) and stirring was continued for further 45 minutes. After that time, the resulting reaction mixture was diluted with dichloromethane (15 ml), the organic layer was separated and the aqueous phase extracted with dichloromethane (3×15 ml). The combined organic portions were dried over magnesium sulphate and evaporated to give a residue which upon distillation under reduced pressure gave 1-oxaspiro[2,5]octane-2-carbonitrile.

Workup

  1. customAfter that time, the resulting reaction mixture
  2. customthe organic layer was separated
  3. extractionthe aqueous phase extracted with dichloromethane (3×15 ml)
  4. dry with materialThe combined organic portions were dried over magnesium sulphate
  5. customevaporated
  6. customto give a residue which
  7. distillationupon distillation under reduced pressure

Sources & evidence

ORD record
ord-56aeb6ba30e14a1f850089e98a5ace7a
Source dataset
uspto-grants-1989_11
Patent number
US04880894

Reaction notes

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