Hydrochloric Acid → 1,3-Dichloro-2-(chloromethyl)-5-nitrobenzene

HRID 746043

Reaktionsgleichung

Reaktionsgleichung von HRID 746043
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Cl:11])[C:3]=1[CH3:12].CO.[Cl:15][O-].[Na+].Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][Cl:15]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2516701,3-Dichloro-2-methyl-5-nitrobenzeneHCID 23665760Sodium Hypochlorite

Produkt 1

HCID 233113981,3-Dichloro-2-(chloromethyl)-5-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2,6-dichloro-4-nitrotoluene (2.0 g 9.7 mmol) in tetrahydrofuran: methanol mixture (20:11 cm3) was added slowly to a vigorously stirred solution of 10-14% aqueous sodium hypochlorite (15 cm3) at 0° C. After 3.75 h at this temperature, the mixture was poured into dilute hydrochloric acid and then extracted with chloroform (30 cm3). The organic extract was dried and evaporated to yield an organge oil which was purified by flash chromatography over silica gel eluting with an ethyl acetate-petroleum ether gradient. The title compound was obtained as a pale orange solid, m.p. 37°-9° C. (1.8 g).

Aufarbeitung

  1. extractionextracted with chloroform (30 cm3)
  2. extractionThe organic extract
  3. customwas dried
  4. customevaporated
  5. customto yield an organge oil which
  6. customwas purified by flash chromatography over silica gel eluting with an ethyl acetate-petroleum ether gradient

Quellen und Nachweise

ORD-Eintrag
ord-adb57b7dbb454cf5aa6ff90823b47a4f
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04602041

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