Thionyl Chloride → HCID 54381910, compound

HRID 1578103Notes

Reaction equation

HRID 1578103 reaction equation
S(Cl)([Cl:3])=O.O[CH:6]=[C:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10]>C1(C)C=CC=CC=1>[Cl:3][CH:6]=[C:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 70528399HCID 70528399, compound

Product 1

HCID 54381910HCID 54381910, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

297.5 g (2.5 mol) of thionyl chloride were stirred slowly into a solution, warmed to 60° C., of 404.6 g (1.7 mol) of 1-hydroxy-2-(4-fluorophenoxy)-4,4-dimethyl-penten-3-one in 3,000 ml of anhydrous toluene. The mixture was kept at the above temperature for 12 hours and then the solvent and excess thionyl chloride were distilled off. The oil which remained was distilled in vacuo. 353.3 g (81% of theory) of 1-chloro-2-(4-fluorophenoxy)-4,4-dimethyl-penten-3-one of boiling point 95°-103° C./0.3 mm Hg were obtained.

Workup

  1. distillationthe solvent and excess thionyl chloride were distilled off
  2. distillationThe oil which remained was distilled in vacuo

Sources & evidence

ORD record
ord-875c1e2add5148daaf53bfbd4cd547b9
Source dataset
uspto-grants-1981_09
Patent number
US04291044

Reaction notes

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