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

HRID 50013

반응식

HRID 50013 반응식
[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]

참가 물질

9

반응물 3

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

생성물 1

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

시약·촉매·용매 5

HCID 23925Iron촉매HCID 313Hydrochloric Acid용매HCID 702Ethanol용매HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c4e4019637dc499c97aa04611feb8ff6
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710077B1

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