Trichloroethylene → HCID 53830804, compound

HRID 1248374Notes

Reaction equation

HRID 1248374 reaction equation
[Cl:1][CH:2]=[C:3]([Cl:5])Cl.[Na].[OH:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12].C(OCCO)C>C(Cl)Cl>[Cl:5][C:3]([O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])=[CH:2][Cl:1]

Participants

6

Reactant 4

HCID 6575TrichloroethyleneHCID 8076Glycol monoethyl etherHCID 88068Methyl 3-HydroxybenzoateHCID 5360545Sodium

Product 1

HCID 53830804HCID 53830804, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

185 parts of trichloroethylene are introduced into a suspension of 180 parts of the sodium salt of methyl 3-hydroxybenzoate in 200 parts of ethylene glycol monoethyl ether in an autoclave, and the mixture is stirred for 2 hours at 150° C. The solvent is then stripped off under reduced pressure, the viscous residue is taken up in 300 parts of methylene chloride and the solution is filtered in the presence of active charcoal and is chromatographed over neutral alumina. After removing the methylene chloride under reduced pressure from the whole eluate, the residue is distilled through a Vigreux column at 125°-131° C./0.6 mbar, giving methyl 3-(1',2'-dichlorovinyloxy)-benzoate, of nD25 =1.5419.

Workup

  1. filtrationthe solution is filtered in the presence of active charcoal
  2. customis chromatographed over neutral alumina
  3. customAfter removing the methylene chloride under reduced pressure from the whole eluate
  4. distillationthe residue is distilled through a Vigreux column at 125°-131° C./0.6 mbar

Sources & evidence

ORD record
ord-a2c01389189c4fb5983e87ffc57ad5f5
Source dataset
uspto-grants-1985_06
Patent number
US04523942

Reaction notes

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