4-Chlorophenol → HCID 13295541, compound

HRID 1731311Notes

Reaction equation

HRID 1731311 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:9][CH2:10][C:11]1([CH2:14]Cl)[CH2:13][O:12]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:9][CH2:10][C:11]1([CH2:14][O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:13][O:12]1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 127317282,2-Bis(chloromethyl)oxirane

Product 1

HCID 13295541HCID 13295541, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

12.85 g (0.1 mol) of 4-chlorophenol in 50 ml of acetone are added dropwise to a mixture of 14.1 g (0.1 mol) of 2,2-di(chloromethyl)-oxirane and 13.8 g (0.1 mol) of potassium carbonate in 200 ml of acetone. The mixture is heated under reflux for 18 hours, left to cool and filtered. The filtrate is concentrated in vacuo, the residue is dissolved in chloroform and the solution is washed with water, dried over sodium sulphate and concentrated. Purification of the residue by distillation gives 7.6 g (32.5% of theory) of 2-chloromethyl-2-(4-chlorophenoxymethyl)-oxirane of boiling point 150° C./0.5 mbar.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 18 hours
  3. waitleft
  4. temperatureto cool
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated in vacuo
  7. dissolutionthe residue is dissolved in chloroform
  8. washthe solution is washed with water
  9. dry with materialdried over sodium sulphate
  10. concentrationconcentrated
  11. customPurification of the residue
  12. distillationby distillation

Sources & evidence

ORD record
ord-2914dfdbb7554be7b2c46a710c35301b
Source dataset
uspto-grants-1986_11
Patent number
US04621095

Reaction notes

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