Acetic Acid → 3-(2,2-Dichlorovinyloxy)-benzaldehyde

HRID 1578124Notes

Reaction equation

HRID 1578124 reaction equation
[Cl:1][C:2]([Cl:13])=[CH:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8]Br.C1N2CN3CN(C2)CN1C3.C(O)(=[O:26])C>O>[Cl:1][C:2]([Cl:13])=[CH:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:26]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 204827061-(Bromomethyl)-3-[(2,2-dichloroethenyl)oxy]benzene

Product 1

HCID 134899763-(2,2-Dichlorovinyloxy)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 8.5 g of 3-(2,2-dichlorovinyloxy)-benzyl bromide in 12.6 ml of acetic acid and 12.6 ml of water are added 8.4 g of hexamethylene tetramine. The resultant solution is refluxed for two hours. Subsequently 10 ml of HC1 are added and the reaction mixture is stirred for half an hour at 100°-110° C. The solution is washed with 100 ml of water and extracted cold (3 times) with 100 ml of ethyl acetate. The extract is washed with sodium carbonate solution and evaporated, to yield 5.8 g of 3-(2,2-dichlorovinyloxy)-benzaldehyde as a yellowish-brown oil, which can be used without further purification.

Workup

  1. additionSubsequently 10 ml of HC1 are added
  2. washThe solution is washed with 100 ml of water
  3. extractionextracted cold (3 times) with 100 ml of ethyl acetate
  4. washThe extract is washed with sodium carbonate solution
  5. customevaporated

Sources & evidence

ORD record
ord-7fe54801ba4f4bdbbb6f73b7ff4eab5f
Source dataset
uspto-grants-1981_09
Patent number
US04291056

Reaction notes

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