Potassium Carbonate → 3-Chloro-6-(1-cyanoethoxy)-benzaldehyde

HRID 267793

Reaction equation

HRID 267793 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:18]([CH3:21])[C:19]#[N:20]>CC(C)=O>[Cl:1][C:2]1[CH:9]=[C:6]([C:5]([O:10][CH:18]([C:19]#[N:20])[CH3:21])=[CH:4][CH:3]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 124815-Chloro-salicylaldehydeHCID 5192252-Chloropropionitrile2×

Product 1

HCID 215539233-Chloro-6-(1-cyanoethoxy)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-chlorosalicylaldehyde (78 g., 0.5 mole), finely powdered anhydrous potassium carbonate (103.5 g., 0.75 mole) and acetone (500 ml.) is stirred under reflux and 2-chloropropionitrile (33.6 g., 0.375 mole) is added over a period of about 5 minutes. The mixture is heated under reflux for 1.5 hours and then treated with potassium carbonate (34.5 g., 0.25 mole) followed by more 2-chloropropionitrile (11.2 g., 0.125 mole). Heating and stirring are continued for 31/2 hours, after which the reaction mixture is filtered and the filter-cake washed with acetone. Evaporation of the combined filtrate gives 3-chloro-6-(1-cyanoethoxy)-benzaldehyde which is recrystallized from aqueous methanol.

Workup

  1. temperatureunder reflux
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 1.5 hours
  4. temperatureHeating
  5. stirringstirring
  6. custom2 hours
  7. filtrationafter which the reaction mixture is filtered
  8. washthe filter-cake washed with acetone
  9. customEvaporation of the combined filtrate

Sources & evidence

ORD record
ord-7a6b98e1ac1041ad9fec417b3c3d37b2
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Linked notes

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