Chloroacetonitrile → 4-Acetonylphenoxyacetonitrile

HRID 465441Notes

Reaction equation

HRID 465441 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]#[N:21]>CC(C)=O>[CH2:8]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:19][C:20]#[N:21])=[CH:7][CH:6]=1)[C:9]([CH3:10])=[O:11]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 70192744-Hydroxyphenylacetone

Product 1

HCID 198745284-Acetonylphenoxyacetonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxyphenylpropan-2-one, ethylene ketal (4.7 g), potassium carbonate (3.5 g) and chloroacetonitrile (1.83 g) in acetone, was heated under reflux for 5 h, cooled, filtered, and treated with 2N hydrochloric acid (1 ml). The solution was allowed to stand at room temperature for 4 h, the solvent was evaporated in vacuo and the residue partitioned between ethylacetate and water. The organic layer was dried, (magnesium sulphate), filtered and evaporated. The residue was purified by column chromatography on silica using chloroform as eluent to give 4-acetonylphenoxyacetonitrile, (3.0 g)

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 h
  3. temperaturecooled
  4. filtrationfiltered
  5. additiontreated with 2N hydrochloric acid (1 ml)
  6. customthe solvent was evaporated in vacuo
  7. customthe residue partitioned between ethylacetate and water
  8. dry with materialThe organic layer was dried, (magnesium sulphate),
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-c1e0f1d154514fb6a91aac39acd4190d
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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