Water → 3-(4-Chloro-3-ethylphenoxy)aniline

HRID 1060060

Reaktionsgleichung

Reaktionsgleichung von HRID 1060060
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([N+:13]([O-])=O)[CH:10]=[CH:11][CH:12]=2)=[CH:4][C:3]=1[CH2:18][CH3:19].O>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[NH2:13])=[CH:4][C:3]=1[CH2:18][CH3:19]

Komponenten

5

Edukt 2

HCID 962WaterHCID 110657543-(4-Chloro-3-ethylphenoxy)-1-nitrobenzene

Produkt 1

HCID 110212303-(4-Chloro-3-ethylphenoxy)anilineAusbeute 112,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

EX-8B) To a solution of 3-(4-chloro-3-ethylphenoxy)-1-nitrobenzene (10 g, 0.036 mol) from EX-A in 400 mL of glacial acetic acid and 1 mL of water was added zinc metal (20 g, 0.305 mol) at room temperature, and the resultant mixture was stirred for 1 h. The reaction mixture was filtered through celite. The filtrate was neutralized with ammonium hydroxide and extracted with diethyl ether. The organic layer was washed with water and brine, dried over MgSO4, and concentrated in vacuo to give 10 g (100%) of the desired 3-(4-chloro-3-ethylphenoxy)aniline product as a dark orange oil, which was greater than 90% pure by reverse phase HPLC analysis. HRMS calcd. for C14H14ClNO: 248.0842 [M+H]+, found: 248.0833.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f20a67beeb5347b0b2a98e1eefd2e43f
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521607B1

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