Acetic Acid → 1-[(2,2-Dichloroethenyl)oxy]-3-methylbenzene

HRID 1578123Notes

Reaction equation

HRID 1578123 reaction equation
[Cl:1][C:2](Cl)([Cl:16])[CH:3](OC(=O)C)[O:4][C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1.C(O)(=O)C>CCCCCC>[Cl:1][C:2]([Cl:16])=[CH:3][O:4][C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 205689273-(2,2,2-Trichloro-1-acetoxy-ethoxy)-toluene

Product 1

HCID 205689261-[(2,2-Dichloroethenyl)oxy]-3-methylbenzene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

71 g of 3-(2,2,2-trichloro-1-acetoxy-ethoxy)-toluene and 150 ml of acetic acid are stirred in a reaction vessel at 35°-45° C. 37 g of zink dust are added subsequently in the course of 2 to 3 minutes and the resultant reaction mixture is stirred for 1 hour at room temperature. The suspension is then mixed with hexane, filtered and washed. Acetic acid is removed by shaking out the organic phase with 2 N NaOH. After evaporation, 43 g 3-(2,2-dichlorovinyloxy)-toluene are obtained as a colourless oil, which can be used for processing without purification.

Workup

  1. addition37 g of zink dust are added subsequently in the course of 2 to 3 minutes
  2. customthe resultant reaction mixture
  3. filtrationfiltered
  4. washwashed
  5. customAcetic acid is removed
  6. stirringby shaking out the organic phase with 2 N NaOH
  7. customAfter evaporation, 43 g 3-(2,2-dichlorovinyloxy)-toluene
  8. customare obtained as a colourless oil, which
  9. customcan be used for processing without purification

Sources & evidence

ORD record
ord-d607af394ae542dcac99aa02ebfe84ad
Source dataset
uspto-grants-1981_09
Patent number
US04291056

Reaction notes

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