Hexane → 4-Chloro-3-(3-methyl-2-butenyloxy)benzenamine

HRID 1939338

Reaktionsgleichung

Reaktionsgleichung von HRID 1939338
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[O:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15].C(OCC)(=O)C.CCCCCC>C(O)C.O.Cl.C(OCC)C.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[O:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15]

Komponenten

9

Edukt 3

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 129856901-Chloro-2-(3-methyl-2-butenyloxy)-4-nitrobenzene

Produkt 1

HCID 129856914-Chloro-3-(3-methyl-2-butenyloxy)benzenamine

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 23925IronKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a refluxing well-stirred suspension of iron powder (19.6 g, 100 mesh) in ethanol (60 mL), water (13.4 mL) and 36% hydrochloric acid (1.4 mL) was added 1-chloro-2-(3-methyl-2-butenyloxy)-4-nitrobenzene (24 g) in portions over 15-30 minutes. After 3 hours thin-layer chromotography (TLC) (ethyl acetate:hexane, 40:60) showed no substrate. The reaction mixture was then filtered hot and the iron oxide filter cake was washed with hot ethanol. The combined ethanol washes were evaporated to produce a residue. The residue was taken up in diethyl ether, washed with aqueous bicarbonate and water, dried (MgSO4), filtered, and evaporated, to give 4-chloro-3-(3-methyl-2-butenyloxy)benzenamine, 19.8 g of light brown oil.

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered hot
  2. filtrationthe iron oxide filter cake
  3. washwas washed with hot ethanol
  4. customThe combined ethanol washes were evaporated
  5. customto produce a residue
  6. washwashed with aqueous bicarbonate and water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-adcec70204ab4bc7b916a2c2eaf51f9a
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05696151

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