MAGNESIUM SILICATE (synthetic) → 2-[(1,2-Dichloroethenyl)oxy]aniline

HRID 985891Notes

Reaction equation

HRID 985891 reaction equation
[Cl:1][C:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O)=[CH:3][Cl:4].[H][H].[O-][Si]([O-])=O.[Mg+2]>C(OCC)(=O)C.C(OCC)(=O)C.CCCCCC.[Pd]>[NH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[O:5][C:2]([Cl:1])=[CH:3][Cl:4]

Participants

7

Reactant 3

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 53865746HCID 53865746, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 543384152-[(1,2-Dichloroethenyl)oxy]anilineYield 89.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Two hundred and eighteen grams of 1,2-dichloro-1-(2-nitrophenoxy)ethene in ethyl acetate with 2.2 g of 10% palladium-on-charcoal was treated with 60 pounds per square inch gauge of hydrogen at 60° until there was no further uptake of hydrogen. The reaction mixture was filtered through Celite® and concentrated in vacuo to yield a brown oil. This oil was taken up in 20% ethyl acetate/hexane and passed through a column of Florisil® two times to yield 169.5 g of oil after evaporation of the solvent.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationconcentrated in vacuo
  3. customto yield a brown oil

Sources & evidence

ORD record
ord-74f1fe69cc0d484591634bff89e23af1
Source dataset
uspto-grants-1987_12
Patent number
USH0000386

Reaction notes

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