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

HRID 50013

Reaction equation

HRID 50013 reaction equation
[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]

Participants

9

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 5

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

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 chromatography (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.

Workup

  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

Sources & evidence

ORD record
ord-c4e4019637dc499c97aa04611feb8ff6
Source dataset
uspto-grants-2004_03
Patent number
US06710077B1

Linked notes

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