Reaction #217451

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
   Extractionthe solution was extracted with toluene
2. 2
   WashThe toluene layer was washed well with water
3. 3
   workup.DISTILLATIONtoluene was distilled off
4. 4
   workup.ADDITIONSodium hydroxide 20 g, water 50 ml and ethanol 200 ml were added to the resulting residue
5. 5
   Temperaturerefluxed for 2 hours
6. 6
   workup.DISTILLATIONEthanol was distilled off
7. 7
   workup.ADDITIONhydrochloric acid was added to the residue
8. 8
   ExtractionThe solution was extracted with diethyl ether
9. 9
   Dryingthe extract was dried on anhydrous magnesium sulfate
10. 10
    OtherA residue obtained
11. 11
    workup.DISTILLATIONby distilling the solvent
12. 12
    Otheroff was recrystallized from a mixed solvent of ethanol and water

Procedure

A dimethylformamide (50 ml) solution of allyl(4-chlorobutyl) ether 14 g, 4-hydroxybenzoic acid 14 g and potassium carbonate 14 g was stirred at 90° C. for 3 hours. Water was added thereto, and the solution was extracted with toluene. The toluene layer was washed well with water, and then toluene was distilled off. Sodium hydroxide 20 g, water 50 ml and ethanol 200 ml were added to the resulting residue and refluxed for 2 hours. Ethanol was distilled off, and then hydrochloric acid was added to the residue to acidify the solution. The solution was extracted with diethyl ether, and the extract was dried on anhydrous magnesium sulfate. A residue obtained by distilling the solvent off was recrystallized from a mixed solvent of ethanol and water to obtain 29 g of 4-(4-allyloxybutyloxy)benzoic acid. Phase transition temperature: C94N107I.

Source