Reaction #6409

Reaction equation

2-methylbutyl p-toluenesulfonate

hydroquinone

sodium hydroxide

→

ether

Yield 72.0%

4-(2-methylbutoxy)phenol

Yield 72.0%

Solvents

n-butanol

water

n-butanol

water

Conditions

Workup

1. 1
   Otherprepared
2. 2
   workup.ADDITIONadded dropwise
3. 3
   workup.DISSOLUTIONdissolved in a solvent mixture
4. 4
   Extractionthe reaction solution was extracted with ether
5. 5
   Otherthe extracted solution was dried
6. 6
   Concentrationconcentrated
7. 7
   ConcentrationThe resulting concentrate
8. 8
   Otherwas purified by column chromatography

Procedure

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%).

Source