Hydrochloric Acid → 2-Tert-butyl-5-methyl-4-nitrosophenol

HRID 985581

Reaktionsgleichung

Reaktionsgleichung von HRID 985581
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].C(O)C.Cl.[N:17]([O-])=[O:18].[Na+]>O>[C:1]([C:5]1[CH:10]=[C:9]([N:17]=[O:18])[C:8]([CH3:11])=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 69376-tert-Butyl-m-cresolHCID 23668193Sodium Nitrite

Produkt 1

HCID 2285202-Tert-butyl-5-methyl-4-nitrosophenolAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-(tert-butyl)-5-methylphenol (32.9 g, 0.2 mol) in water:ethanol (300 ml, 2:1) was added concentrated hydrochloric acid (20 ml, 0.24 mol) and then cooled to 0° C. To the solution was added dropwise a solution of sodium nitrite (14.5 g, 0.21 mol) in water (40 ml) over 30 minutes. After completing the dropwise addition, the mixture was stirred at the same temperature for 2 hours. The precipitated crystals were collected by a filtration, and washed with a cold water. The resultant crystal was dissolved in an ethyl acetate:THF (9:1) solution, washed with saturated brine, dried over sodium sulfate, and purified by silica gel column chromatography on a small amount of silica gel which was eluted with ethyl acetate. After the solvent was removed under reduced pressure, the residue was suspended in hexane and the crystals were collected by filtration to obtain 31.4 g of the title compound.

Aufarbeitung

  1. additionthe dropwise addition
  2. filtrationThe precipitated crystals were collected by a filtration
  3. washwashed with a cold water
  4. dissolutionThe resultant crystal was dissolved in an ethyl acetate:THF (9:1) solution
  5. washwashed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. custompurified by silica gel column chromatography on a small amount of silica gel which
  8. washwas eluted with ethyl acetate
  9. customAfter the solvent was removed under reduced pressure
  10. filtrationthe crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-b1bf1b1509e24a439da990ed08530383
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06872718B1

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