Reaction #1121716

Reaction equation

hydroquinone

1,6-dibromo hexane

Potassium hydroxide

→

4-(6-bromohexyloxy)phenol

Yield 39.4%

Solvents

methanol

Conditions

Workup

1. 1
   Otherfluxed at 60° C.
2. 2
   Other(Celsius) overnight
3. 3
   Otheris lowered to a room temperature
4. 4
   Othermethanol was evaporated from the reaction mixture
5. 5
   ExtractionThen, the reaction mixture was extracted three times with water (100 ml (milliliters)) and ethyl acetate (100 ml (milliliters))
6. 6
   OtherWater was removed over magnesium sulfate
7. 7
   Otherthe solvents were evaporated
8. 8
   Otherthe resulting reaction mixture
9. 9
   Otherwas purified

Procedure

As shown in the following Scheme, hydroquinone (1) (4.5 g (grams)) and 1,6-dibromo hexane (2) (10 g (grams)) were dissolved in methanol (100 ml (milliliters)) at a room temperature. Potassium hydroxide (2.3 g (grams)) was added to the resulting mixture solution, and then fluxed at 60° C. (Celsius) overnight. Next day, the temperature of the reaction mixture is lowered to a room temperature, and methanol was evaporated from the reaction mixture. Then, the reaction mixture was extracted three times with water (100 ml (milliliters)) and ethyl acetate (100 ml (milliliters)). Water was removed over magnesium sulfate, and the solvents were evaporated, and the resulting reaction mixture was purified using a column chromatography (developer solution: ethylacetate/hexane=1/5 volume ratio) to obtain 4.4 g (grams) of 4-(6-bromohexyloxy)phenol (3).

Source