Sulfuryl chloride → 4-n-Butoxy-3-chloro-1,1,1-trifluorobut-3-en-2-one

HRID 2352412Notes

Reaction equation

HRID 2352412 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH2:6]([O:10][CH:11]=[CH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:7][CH2:8][CH3:9]>ClCCl>[CH2:6]([O:10][CH:11]=[C:12]([Cl:4])[C:13](=[O:18])[C:14]([F:16])([F:17])[F:15])[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 2782641Butoxyvinyl trifluoromethyl ketone

Product 1

HCID 544484544-n-Butoxy-3-chloro-1,1,1-trifluorobut-3-en-2-oneYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

28.0 g (0.22 mole) of sulphuryl chloride in 60 ml of dichloromethane are added dropwise with stirring to 39.0 g (0.2 mole) of 4-n-butoxy-1,1,1-trifluoro-but-3-en-2-one in 200 ml of dichloromethane at 0° C. After stirring for 4 hours at 0° C., the solvent and unreacted sulphuryl chloride are distilled off and the residue is distilled slowly under reduced pressure. 42.5 g of pale yellow 4-n-butoxy-3-chloro-1,1,1-trifluorobut-3-en-2-one of boiling point 105°-106° C./12 mbar, nD20 =1.4484 are obtained.

Workup

  1. distillationthe solvent and unreacted sulphuryl chloride are distilled off
  2. distillationthe residue is distilled slowly under reduced pressure

Sources & evidence

ORD record
ord-0192ec466e904ec8b0dafeb7a17b6637
Source dataset
uspto-grants-1989_10
Patent number
US04876393

Reaction notes

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