4-Hydroxybenzoic Acid → 4-(4-Allyloxybutyloxy)benzoic acid

HRID 490033Notes

Reaction equation

HRID 490033 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8]Cl)[CH:2]=[CH2:3].[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 137481731-Chloro-4-[(prop-2-en-1-yl)oxy]butane

Product 1

HCID 219606264-(4-Allyloxybutyloxy)benzoic acidYield 123%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A reaction mixture containing 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 the reaction mixture, which was then extracted with toluene. The toluene layer was well washed with water, and then toluene was distilled off. 20 g of sodium hydroxide, 50 mL of water and 200 mL of ethanol were added to the resulting residue, followed by refluxing for 2 hours. Ethanol was distilled off, and hydrochloric acid was added to make the reaction mixture acidic. The mixture was extracted with diethyl ether and dried over anhydrous magnesium sulfate. A residue obtained by distilling the solvent was recrystallized from a mixed solvent of ethanol and water to obtain 29 g of 4-(4-allyloxybutyloxy)benzoic acid.

Workup

  1. extractionwas then extracted with toluene
  2. washThe toluene layer was well washed with water
  3. distillationtoluene was distilled off
  4. addition20 g of sodium hydroxide, 50 mL of water and 200 mL of ethanol were added to the resulting residue
  5. temperatureby refluxing for 2 hours
  6. distillationEthanol was distilled off
  7. additionhydrochloric acid was added
  8. extractionThe mixture was extracted with diethyl ether
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customA residue obtained
  11. distillationby distilling the solvent
  12. customwas recrystallized from a mixed solvent of ethanol and water

Sources & evidence

ORD record
ord-a0fdedeffaa44540bf2c29be6664c1cd
Source dataset
uspto-grants-2009_05
Patent number
US07527746B2

Reaction notes

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