Chloroacetonitrile → HCID 21553961, compound

HRID 267795Notes

Reaction equation

HRID 267795 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:13])[C:5]([O:8][CH:9]([C:11]#[N:12])[CH3:10])=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][C:22]#[N:23]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([O:8][CH:9]([C:11]#[N:12])[CH3:10])=[CH:6][CH:7]=1)[O:13][CH2:21][C:22]#[N:23]

Participants

5

Reactant 3

HCID 7856Chloroacetonitrile2×HCID 11430Potassium Carbonate2×HCID 21553948HCID 21553948, compound

Product 1

HCID 21553961HCID 21553961, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-chloro-6-(1-cyanoethoxy)-phenol (34.6 g., 0.175 mole), finely powdered anhydrous potassium carbonate (37.2 g., 0.27 mole) and acetone (250 ml.) is stirred under reflux while chloroacetonitrile (9.8 g., 0.13 mole) is added over a period of about 5 minutes. The mixture then is heated under reflux with vigorous stirring for 1.5 hours, whereupon more potassium carbonate (12.5 g., 0.09 mole) and chloroacetonitrile (3.4 g., 0.045 mole) are added. Stirring and heating are continued for 3.5 hours, then the mixture is filtered and the filter-cake washed with acetone. Evaporation of the combined filtrate affords 3-chloro-6-(1-cyanoethoxy)-phenoxyacetonitrile which is recrystallized from aqueous alcohol.

Workup

  1. additionis added over a period of about 5 minutes
  2. temperatureThe mixture then is heated
  3. temperatureunder reflux
  4. additionare added
  5. stirringStirring
  6. temperatureheating
  7. filtrationthe mixture is filtered
  8. washthe filter-cake washed with acetone
  9. customEvaporation of the combined filtrate

Sources & evidence

ORD record
ord-9a6d7917b0274420b6fa4f97cc1a398a
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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