Reaction #2069931

Reaction equation

dimethylformamide

allyl (4-chlorobutyl) ether

4-hydroxybenzoic acid

potassium carbonate

→

4-(4-allyloxybutyloxy)benzoic acid

Yield 123.0%

Solvents

Water

Conditions

Workup

1. 1
   Extractionextracted with toluene
2. 2
   Washthe toluene layer was well washed with water, and toluene
3. 3
   Otherwas evaporated away
4. 4
   workup.ADDITION20 g of sodium hydroxide, 50 ml of water and 200 ml of ethanol were added to the resulting residue
5. 5
   Temperaturerefluxed for 2 hours
6. 6
   OtherEthanol was evaporated away
7. 7
   workup.ADDITIONhydrochloric acid was added
8. 8
   Extractionextracted with diethyl ether
9. 9
   Dryingdried with anhydrous magnesium sulfate
10. 10
    OtherThe solvent was evaporated away
11. 11
    Otherthe resulting residue was recrystallized from a mixed solvent of ethanol and water

Procedure

A solution comprising 14 g of allyl (4-chlorobutyl) ether, 14 g of 4-hydroxybenzoic acid, 14 g of potassium carbonate and 50 ml of dimethylformamide was stirred at 90° C. for 3 hours. Water was added to it, and extracted with toluene, and the toluene layer was well washed with water, and toluene was evaporated away. 20 g of sodium hydroxide, 50 ml of water and 200 ml of ethanol were added to the resulting residue, and refluxed for 2 hours. Ethanol was evaporated away, and hydrochloric acid was added to make it acidic, and then extracted with diethyl ether and dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the resulting residue was recrystallized from a mixed solvent of ethanol and water to obtain 29 g of 4-(4-allyloxybutyloxy)benzoic acid.

Source