Reaktion #6415

Reaktionsgleichung

sodium hydroxide

2-methylbutyl p-toluenesulfonate

hydroquinone

→

4-(2-methylbutoxy)phenol

Ausbeute 72.0%

Lösungsmittel

water

water

n-butanol

n-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   workup.ADDITIONadded dropwise
3. 3
   Extraktionthe reaction solution was extracted with ether
4. 4
   Sonstigethe extracted solution was dried
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe concentrate was purified by column chromatography
7. 7
   Sonstigeto obtain 4.8 g of the objective ether compound

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 of 3 ml of water and 10 ml of n-butanol. After conclusion of the dropping, the 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 concentrate was purified by column chromatography, to obtain 4.8 g of the objective ether compound. (Yield: 72%)

Quelle