Thionyl Chloride → HCID 54381910, compound

HRID 2198897Notes

Reaction equation

HRID 2198897 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 mols) of thionyl chloride were slowly stirred into a solution, warmed to 60° C., of 404.6 g (1.7 mols) of 1-hydroxy-2-(4-fluorophenoxy)-4,4-dimethyl-1-penten-3-one in 3,000 ml of anhydrous toluene. The mixture was kept at this temperature for 12 hours and the solvent and excess thionyl chloride were then 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-1-penten-3-one of boiling point 95°-103° C./0.3 mm Hg were obtained. ##STR51##

Workup

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

Sources & evidence

ORD record
ord-92729a57519b4af6a783e6f96d7979ef
Source dataset
uspto-grants-1982_11
Patent number
US04360528

Reaction notes

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