Reaction #1513

Reaction equation

hydrochloric acid

4'-hydroxybiphenyl-4-carboxylic acid

n-decyl bromide

potassium hydroxide

sodium iodide

potassium hydroxide

→

4'-decyloxybiphenyl-4-carboxylic acid

Yield 6.0%

Solvents

water

water

ethanol

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperaturethe mixture was further heated
3. 3
   Temperatureunder reflux for 2 hours
4. 4
   Temperatureto cool up to room temperature
5. 5
   OtherThe deposited product was separated by filtration
6. 6
   workup.DISSOLUTIONdissolved in acetone
7. 7
   Temperaturewith heating
8. 8
   Filtrationfollowed by filtration
9. 9
   ConcentrationThe resulting filtrate was concentrated

Procedure

A mixture of 21.4 g (0.1 mol) of 4'-hydroxybiphenyl-4-carboxylic acid, 33.15 g (0.15 mol) of n-decyl bromide, 13.20 g (0.2 mol) of 85% potassium hydroxide, 1.05 g (7 mmol) of sodium iodide, 500 ml of ethanol and 100 ml of distilled water was heated under reflux at 100° C. for 12 hours. After 40 ml of 25% potassium hydroxide was added, the mixture was further heated under reflux for 2 hours. After allowing the reaction system to cool up to room temperature, the reaction mixture in cold water was acidified with 36% hydrochloric acid. The deposited product was separated by filtration and dissolved in acetone with heating, followed by filtration. The resulting filtrate was concentrated to obtain 1.97 g (6 mmol) of 4'-decyloxybiphenyl-4-carboxylic acid.

Source