Potassium Carbonate → 2-(4-Chloro-2-cyanophenoxy)-2-methylpropanal

HRID 1655080Notes

Reaction equation

HRID 1655080 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15]#[N:16])[CH:9]=1.Br[C:18]([CH3:22])([CH3:21])[CH:19]=[O:20]>C1COCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:18]([CH3:22])([CH3:21])[CH:19]=[O:20])=[C:10]([C:15]#[N:16])[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5783772-Bromo-2-methylpropanalHCID 27774205-Chloro-2-hydroxybenzonitrile

Product 1

HCID 200775612-(4-Chloro-2-cyanophenoxy)-2-methylpropanalYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
4 °C

Procedure

Anhydrous potassium carbonate (2.76 g) was added to a stirred solution of 4-chloro-2-cyanophenol (1.53 g) and 2-bromo-2-methyl propanal (2.26 g) in THF (50 ml) and the mixture heated at reflux for 5 hours. The mixture was then cooled to 4° C., the suspended solid removed by filtration and the filtrate evaporated to give a yellow oil which crystallised on standing. The solid was triturated with hexane and collected by filtration to give 2-(4-chloro-2-cyanophenoxy)-2-methylpropanal (2.11 g), m.p. 85°-88° C.;

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 5 hours
  3. customthe suspended solid removed by filtration
  4. customthe filtrate evaporated
  5. customto give a yellow oil which
  6. customcrystallised
  7. customThe solid was triturated with hexane
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-52f53f59bb2c4310985daf7ebe8ac533
Source dataset
uspto-grants-1995_04
Patent number
US05410064

Reaction notes

Loading…