Reaktion #6409

Reaktionsgleichung

2-methylbutyl p-toluenesulfonate

hydroquinone

sodium hydroxide

→

ether

Ausbeute 72.0%

4-(2-methylbutoxy)phenol

Ausbeute 72.0%

Lösungsmittel

n-butanol

water

n-butanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   workup.ADDITIONadded dropwise
3. 3
   workup.DISSOLUTIONdissolved in a solvent mixture
4. 4
   Extraktionthe reaction solution was extracted with ether
5. 5
   Sonstigethe extracted solution was dried
6. 6
   Einengenconcentrated
7. 7
   EinengenThe resulting concentrate
8. 8
   Sonstigewas purified by column chromatography

Vorschrift

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%).

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