Ethanol → 1-Chloro-5-(4-chlorophenoxy)-3,3-dimethylpentan-2-one

HRID 569199Notes

Reaction equation

HRID 569199 reaction equation
[Cl:1][C:2](OC1C=CC(Cl)=CC=1)=[CH:3][C:4]([CH3:16])([CH3:15])[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.C([OH:27])C>Cl>[Cl:1][CH2:2][C:3](=[O:27])[C:4]([CH3:16])([CH3:15])[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 54255953HCID 54255953, compound

Product 1

HCID 133228741-Chloro-5-(4-chlorophenoxy)-3,3-dimethylpentan-2-oneYield 88%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

580 g (1.5 mols) of 1-chloro-3,3-dimethyl-1,5-di-(4-chlorophenoxy)-1-pentene in 1,000 ml of ethanol and 300 ml of concentrated hydrochloric acid are heated under reflux for 4 hours. The ethanol is removed in vacuo, and the residue is diluted with methylene chloride and extracted by shaking with water, and then three times with dilute sodium hydroxide solution. The dried solution is freed of solvent in vacuo. 363 g (88% of theory) of 1-chloro-5-(4-chlorophenoxy)-3,3-dimethyl-2-pentanone are obtained as an oil.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe ethanol is removed in vacuo
  3. additionthe residue is diluted with methylene chloride
  4. extractionextracted

Sources & evidence

ORD record
ord-d66122ce2dde4cf5be909e71f315066e
Source dataset
uspto-grants-1988_03
Patent number
US04731452

Reaction notes

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