2,3-Dichloropropene → HCID 14819356, compound

HRID 330285Notes

Reaction equation

HRID 330285 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:15][C:16]([CH2:18]Cl)=[CH2:17]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][C:16]([Cl:15])=[CH2:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 65652,3-DichloropropeneHCID 97324-FluorophenolHCID 11430Potassium Carbonate

Product 1

HCID 14819356HCID 14819356, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

According to the procedure of W. K. Anderson et al., J. Chem. Soc., Perkin 1,1 (1976), a mixture of 4-fluorophenol (20.0 g, 0.178 mol) and K2CO3 (27.3 g, 0.196 mol) in acetone (250 mL) was heated at reflux for 1 hour. 2,3-Dichloro-1-propene was added, and the resulting mixture was refluxed for 2 days, cooled, and concentrated. The mixture was diluted with H2O, and extracted with ether (3×150 mL). The ethereal extracts were dried (MgSO4) and concentrated to give a brown oil. Distillation under high vacuum gave 26.4 g (79%) of product as a colorless liquid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperaturethe resulting mixture was refluxed for 2 days
  4. temperaturecooled
  5. concentrationconcentrated
  6. additionThe mixture was diluted with H2O
  7. extractionextracted with ether (3×150 mL)
  8. dry with materialThe ethereal extracts were dried (MgSO4)
  9. concentrationconcentrated
  10. customto give a brown oil
  11. distillationDistillation under high vacuum

Sources & evidence

ORD record
ord-0889d291dbb4401680730b9cf407a9a0
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

Loading…