Sulfuric Acid → 5-Ethyl-2-nitrophenol

HRID 323095

Reaktionsgleichung

Reaktionsgleichung von HRID 323095
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)[CH3:2].[N+:10]([O-])([O-:12])=[O:11].[Na+].S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(Cl)Cl>[N+:10]([C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][C:5]=1[OH:9])([O-:12])=[O:11]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 121013-EthylphenolHCID 24268Sodium NitrateHCID 23668193Sodium Nitrite

Produkt 1

HCID 155967145-Ethyl-2-nitrophenolAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3-ethylphenol (5.00 g, 41 mmol) was dissolved in methylene chloride(40 mL) followed by the addition of sodium nitrate (3.83 g, 45 mmol). The addition of sulfuric acid (50 mL/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hours, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2Cl2) gave the desired product(1.7 g, 25%). 1H NMR (CD3COCD3): d 8.02 (d,1H), 6.99 (s,1H), 6.85 (d, 1H), 2.69 (q, 2H), 1.30 (t, 3H).

Aufarbeitung

  1. extractionextracted with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-1883fa5fc1824aad9eaa41453274a991
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211373B1

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