Hydroquinone → Phenol, 4-(2-methylbutoxy)-

HRID 6313

Reaktionsgleichung

Reaktionsgleichung von HRID 6313
[C:1]1([CH3:16])[CH:6]=CC(S(OCC(C)CC)(=O)=O)=[CH:3][CH:2]=1.[C:17]1([CH:24]=[CH:23][C:21]([OH:22])=[CH:20][CH:19]=1)[OH:18].[OH-].[Na+]>O.C(O)CCC>[CH3:6][CH:1]([CH2:2][CH3:3])[CH2:16][O:18][C:17]1[CH:24]=[CH:23][C:21]([OH:22])=[CH:20][CH:19]=1

Komponenten

6

Edukt 3

HCID 785HydroquinoneHCID 14798Sodium HydroxideHCID 3011991-Butanol, 2-methyl-, 1-(4-methylbenzenesulfonate)

Produkt 1

HCID 106720Phenol, 4-(2-methylbutoxy)-Ausbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittel2×HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Into a n-butanol suspension containing 37 mmol (9.0 g) of 2-methylbutyl p-toluenesulfonate prepared by tosylating S-(-)-2-methylbutanol and 74 mmol (8.2 g) of hydroquinone, added dropwise was a solution of 50 mmol (2.1 g) of sodium hydroxide dissolved in a solvent mixture comprising 3 ml of water and 10 ml of n-butanol, and the obtained mixture was then stirred for 8 hours at 120° C. After addition of water, the reaction solution was extracted with ether, and the extracted solution was dried and concentrated. The resulting concentrate was purified by column chromatography to obtain 4.8 g of the objective ether compound (Yield: 72%).

Aufarbeitung

  1. customprepared
  2. additionadded dropwise
  3. dissolutiondissolved in a solvent mixture
  4. extractionthe reaction solution was extracted with ether
  5. customthe extracted solution was dried
  6. concentrationconcentrated
  7. concentrationThe resulting concentrate
  8. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ee68d39c5e5542ca8e4b4663ce20dbb7
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248446

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