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

HRID 2211571Notes

Reaction equation

HRID 2211571 reaction equation
ClC[CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10]Cl.[OH:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)[CH:4]=[CH2:3]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 22800Butane, 1,1'-oxybis(4-chloro-

Product 1

HCID 219606264-(4-Allyloxybutyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

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 thereto, and the liquid was extracted with toluene. The toluene layer was washed well with water, and toluene was distilled off. Sodium hydroxide 20 g, water 50 ml and ethanol 200 ml were added to the resulting residue, and the solution was refluxed for 2 hours. Ethanol was distilled off, and hydrochloric acid was added to acidify the solution. It was extracted with diethyl ether and dried on anhydrous magnesium sulfate. The solvent was distilled off, and a residue thus obtained was recrystallized from a mixed solvent of ethanol and water to obtain 29 g of 4-(4-allyloxybutyloxy)benzoic acid. Phase transition temperature: C 94 N 107 I

Workup

  1. extractionthe liquid was extracted with toluene
  2. washThe toluene layer was washed well with water, and toluene
  3. distillationwas distilled off
  4. additionSodium hydroxide 20 g, water 50 ml and ethanol 200 ml were added to the resulting residue
  5. temperaturethe solution was refluxed for 2 hours
  6. distillationEthanol was distilled off
  7. additionhydrochloric acid was added
  8. extractionIt was extracted with diethyl ether
  9. dry with materialdried on anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off
  11. customa residue thus obtained
  12. customwas recrystallized from a mixed solvent of ethanol and water

Sources & evidence

ORD record
ord-092cbb788c544e129f2ca9fbba18a7fd
Source dataset
uspto-grants-2006_09
Patent number
US07101595B2

Reaction notes

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