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

HRID 130269Notes

Reaction equation

HRID 130269 reaction equation
CN(C)C=O.[CH2:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13]Cl)[CH:7]=[CH2:8].[OH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)[CH:7]=[CH2:8]

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

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.

Workup

  1. extractionthe solution was extracted with toluene
  2. washThe toluene layer was washed well with water
  3. distillationtoluene was distilled off
  4. additionSodium hydroxide 20 g, water 50 ml and ethanol 200 ml were added to the resulting residue
  5. temperaturerefluxed for 2 hours
  6. distillationEthanol was distilled off
  7. additionhydrochloric acid was added to the residue
  8. extractionThe solution was extracted with diethyl ether
  9. dry with materialthe extract was dried on anhydrous magnesium sulfate
  10. customA residue obtained
  11. distillationby distilling the solvent
  12. customoff was recrystallized from a mixed solvent of ethanol and water

Sources & evidence

ORD record
ord-c4e2dfceb9af48f38c8dce42e18a34a7
Source dataset
uspto-grants-2008_06
Patent number
US07381350B2

Reaction notes

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