Sulfuryl chloride → 1-([1,1′-Biphenyl]-4-yloxy)-1-chloro-3,3-dimethyl-2-butanone

HRID 972750Notes

Reaction equation

HRID 972750 reaction equation
[C:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH2:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:24])(=O)=O>C(Cl)Cl>[Cl:24][CH:12]([O:11][C:10]1[CH:9]=[CH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:20][CH:19]=1)[C:13](=[O:18])[C:14]([CH3:16])([CH3:17])[CH3:15]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 230504261-([1,1′-Biphenyl]-4-yloxy)-3,3-dimethyl-2-butanone

Product 1

HCID 150706801-([1,1′-Biphenyl]-4-yloxy)-1-chloro-3,3-dimethyl-2-butanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,292 g (4.83 moles) of 1-(4'-phenyl-phenoxy)-3,3-dimethylbutan-2-one were dissolved in 2.5 l of methylene chloride and 400 ml (4.9 moles) of sulfuryl chloride were added dropwise at the boil. The mixture was heated under reflux for 15 hours and was then concentrated by distilling off the solvent. After adding 250 ml of carbon tetrachloride, the solvent was again distilled off under a water-pump vacuum (bath temperature 65° C.). Crude 1-chloro-1-(4'-phenyl-phenoxy)-3,3-dimethylbutan-2-one was obtained quantitatively, and was used further in the form obtained. ##STR3##

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. concentrationwas then concentrated
  4. distillationby distilling off the solvent
  5. additionAfter adding 250 ml of carbon tetrachloride
  6. distillationthe solvent was again distilled off under a water-pump vacuum (bath temperature 65° C.)

Sources & evidence

ORD record
ord-b2e693431eb244a193848d0f447126be
Source dataset
uspto-grants-1977_10
Patent number
US04053616

Reaction notes

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