p-Toluenesulfonic acid → Allyl chlorodifluoroacetate

HRID 329817

Reaction equation

HRID 329817 reaction equation
[Cl:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8](O)[CH:9]=[CH2:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C(Cl)(Cl)Cl>[Cl:1][C:2]([F:7])([F:6])[C:3]([O:5][CH2:10][CH:9]=[CH2:8])=[O:4]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7858Allyl AlcoholHCID 66154Chlorodifluoroacetic acid

Product 1

HCID 10012339Allyl chlorodifluoroacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

In a 1.5 liter sulfonation flask with a water separator, 294.0 g (2.25 mol) of chlorodifluoroacetic acid (pure, from Fluka AG) and 228.0 g (3.93 mol) of allyl alcohol are dissolved in 1 liter of chloroform and kept under reflux for 17 hours in the presence of 11.25 g of p-toluenesulfonic acid (0.06 mol), 41 ml of H2O separating out. The yellow reaction solution is washed twice with H2O and 3 times with saturated aqueous NaHCO3 solution, dried over MgSO4 and distilled under normal pressure through a Vigreux column. Yield: 306.0 g (80%) of a colourless oil of boiling point 98°-100° C./988 mbar.

Workup

  1. washThe yellow reaction solution is washed twice with H2O and 3 times with saturated aqueous NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. distillationdistilled under normal pressure through a Vigreux column

Sources & evidence

ORD record
ord-72a6fd8c9a07476bb8fa95545f96406d
Source dataset
uspto-grants-1990_01
Patent number
US04892962

Linked notes

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