Trichloroacetyl chloride → 4-Trichloroacetoxystyrene

HRID 1873106Notes

Reaction equation

HRID 1873106 reaction equation
C([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)(=O)C.[Cl:13][C:14]([Cl:19])([Cl:18])[C:15](Cl)=[O:16]>[OH-].C[N+](C)(C)C.C(Cl)Cl>[Cl:13][C:14]([Cl:19])([Cl:18])[C:15]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)=[O:16]

Participants

5

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 758214-Ethenylphenyl acetate

Product 1

HCID 154524664-TrichloroacetoxystyreneYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 60966Tetramethylammonium hydroxideSolvent

Conditions

Temperature
5 °C

Procedure

About 10.0 gs (6.17×10-2 moles of 4-acetoxystyrene was dissolved in 42.5 mL of 25 wt % tetramethylammonium hydroxide with stirring. The solution was cooled to 5° C. and to it was added 12.63 gs (6.95×10-2 moles) of trichloracetyl chloride dissolved in 150 mL of methylene chloride. The addition was done slowly with stirring while cooling with an ice bath so as to avoid heating the reaction mixture above 15° C. After 15 mins. of reaction, workup was done by separating the methylene chloride layer, washing it with 3×40 mL of 6 wt % tetramethylammonium hydroxide and several 40 mL aliquots of distilled water. The washed organic layer was dried over magnesium sulphate, filtered over silica gel, and the solvent removed under vacuum. The residue was recrystallized from pet ether to give 10.2 gs (62% yield) of 4-trichloroacetoxystyrene.

Workup

  1. additionThe addition
  2. stirringwith stirring
  3. temperaturewhile cooling with an ice bath so as
  4. temperatureto avoid heating the reaction mixture above 15° C
  5. customof reaction, workup
  6. customby separating the methylene chloride layer
  7. washwashing it with 3×40 mL of 6 wt % tetramethylammonium hydroxide and several 40 mL aliquots of distilled water
  8. dry with materialThe washed organic layer was dried over magnesium sulphate
  9. filtrationfiltered over silica gel
  10. customthe solvent removed under vacuum
  11. customThe residue was recrystallized from pet ether

Sources & evidence

ORD record
ord-eb833c4ad8c3481ba01ca75a01ea2d57
Source dataset
uspto-grants-2000_08
Patent number
US06111133

Reaction notes

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