Sulfuric Acid → 3-Methoxy-4-methylphenol

HRID 527720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527720
[CH3:1][C:2]1[CH:8]=[CH:7][C:5](N)=[CH:4][C:3]=1[O:9][CH3:10].[OH:11]S(O)(=O)=O.N([O-])=O.[Na+]>O>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([OH:11])=[CH:4][C:3]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 1118Sulfuric Acid2×HCID 278823-Methoxy-4-methylanilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 151030153-Methoxy-4-methylphenolAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 4-methyl-3-(methyloxy)aniline (Reference Intermediate R1, 1.86 g) in water (100 mL)/H2SO4 (30 mL, 563 mmol) at 0° C. a solution of sodium nitrite (1.029 g, 14.91 mmol) in water (10 mL) was slowly added and the reaction mixture was stirred for 30 minutes at 0° C. The reaction mixture was slowly added to a solution of H2SO4 98% (20 mL) in Water (80 mL) pre-heated at 90° C. and stirred at this temperature for 1 h. After cooling the mixture was extracted with Et2O (2×200 mL), the organic layer was dried on sodium sulphate, filtered and evaporated to afford the title compound (1.86 g) as a red/brown oil.

Aufarbeitung

  1. additionwas slowly added
  2. temperaturepre-heated at 90° C.
  3. stirringstirred at this temperature for 1 h
  4. temperatureAfter cooling the mixture
  5. extractionwas extracted with Et2O (2×200 mL)
  6. customthe organic layer was dried on sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-833c15f3c34c420b84f84d9cd095ea49
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346790B2

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