Acetyl chloride → 2,2,2-Trichloro-1-(3,4-dichlorophenyl)ethyl acetate

HRID 1704781Notes

Reaction equation

HRID 1704781 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[O:5]=[CH:6][C:7]([Cl:10])([Cl:9])[Cl:8].C(Cl)(=O)C.C(O[C:19](=[O:21])[CH3:20])(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+].[Cl:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[Cl:36]>>[C:19]([O:5][CH:6]([C:33]1[CH:34]=[CH:35][C:30]([Cl:29])=[C:31]([Cl:36])[CH:32]=1)[C:7]([Cl:10])([Cl:9])[Cl:8])(=[O:21])[CH3:20]

Participants

7

Reactant 6

HCID 6367Acetyl chlorideHCID 6407ChloralHCID 72391,2-Dichlorobenzene2×HCID 7918Acetic AnhydrideHCID 24436Sodium SulfateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 890402,2,2-Trichloro-1-(3,4-dichlorophenyl)ethyl acetateYield 92%

Conditions

Temperature
0 °C

Procedure

134 g (1 mole) of aluminum chloride are added, while stirring, to 500 ml (4.4 moles) of o-dichlorobenzene, the excess of which simultaneously serves as the solvent. The mixture is cooled to 0° C and 147.5 g (1 mole) of anhydrous chloral are added dropwise at 0° to 5° C. The mixture is allowed to react further at 0° to 5° C for 6 hours and 78 g (1 mole) of acetyl chloride (or 102 g, 1 mole of acetic anhydride) are then added dropwise at 0° to 8° C. The batch is then poured in portions into a suspension of 322 g (1 mole) of sodium sulfate ·10 H2O in o-dichlorobenzene and the temperature is kept at about 20° C by cooling. The salts which have precipitated out are filtered off and washed twice with 300 ml of o-dichlorobenzene and the solvent is stripped off at 100° C in a rotary evaporator. 100 ml of isopropanol are added to the residue and the mixture is left to crystallize out at 0° C. The crystals are filtered off, washed with a little cold isopropanol and dried in a vacuum desiccator. 309 g (92% of theory) of 1-(3,4-dichlorophenyl)-2,2,2-trichloro-ethyl acetate with a melting point of 85°-86° C are obtained.

Workup

  1. customto react further at 0° to 5° C for 6 hours
  2. customis kept at about 20° C
  3. temperatureby cooling
  4. customThe salts which have precipitated out
  5. filtrationare filtered off
  6. washwashed twice with 300 ml of o-dichlorobenzene
  7. customthe solvent is stripped off at 100° C in a rotary evaporator
  8. addition100 ml of isopropanol are added to the residue
  9. waitthe mixture is left
  10. customto crystallize out at 0° C
  11. filtrationThe crystals are filtered off
  12. washwashed with a little cold isopropanol
  13. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-0200fc447fd04497b82baf0414d92df5
Source dataset
uspto-grants-1978_11
Patent number
US04127728

Reaction notes

Loading…