Acetone → 2-(2-Hydroxyphenoxy)acetonitrile

HRID 267791

Reaction equation

HRID 267791 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].Cl[CH2:10][C:11]#[N:12].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>[OH-].[Na+]>[OH:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][CH2:10][C:11]#[N:12]

Participants

6

Reactant 4

HCID 180AcetoneHCID 289CatecholHCID 7856Chloroacetonitrile2×HCID 11430Potassium Carbonate2×

Product 1

HCID 215539352-(2-Hydroxyphenoxy)acetonitrile

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of catechol (11 g., 0.1 mole), chloroacetonitrile (5.3 g., 0.07 mole), finely powdered potassium carbonate (11.1 g., 0.08 mole) and acetone (75 ml.) is refluxed with stirring for 2 hours. The mixture then is treated with chloroacetonitrile (3.8 g., 0.05 mole) and potassium carbonate (7.6 g., 0.055 mole) and refluxed for 4 hours. The mixture is filtered, the solids washed with more acetone and the combined filtrate evaporated in vacuo to give an oil. The oil is dissolved in dilute sodium hydroxide solution, extracted with ether to remove 1,2-dicyanomethoxybenzene and the alkali solution acidified and extracted with ether. The extract is evaporated to dryness and the residue distilled in vacuo to give 2-(2-hydroxyphenoxy)acetonitrile.

Workup

  1. temperatureis refluxed
  2. temperaturerefluxed for 4 hours
  3. filtrationThe mixture is filtered
  4. washthe solids washed with more acetone
  5. customthe combined filtrate evaporated in vacuo
  6. customto give an oil
  7. extractionextracted with ether
  8. customto remove 1,2-dicyanomethoxybenzene
  9. extractionextracted with ether
  10. customThe extract is evaporated to dryness
  11. distillationthe residue distilled in vacuo

Sources & evidence

ORD record
ord-5d2dd9026d9f46e4b620291df65eff2a
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Linked notes

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