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

HRID 1982749Notes

Reaction equation

HRID 1982749 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH:8]=[CH2:9].[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>[CH2:7]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)[CH:8]=[CH2:9]

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 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.

Workup

  1. extractionextracted with toluene
  2. washthe toluene layer was well washed with water, and toluene
  3. customwas evaporated away
  4. addition20 g of sodium hydroxide, 50 ml of water and 200 ml of ethanol were added to the resulting residue
  5. temperaturerefluxed for 2 hours
  6. customEthanol was evaporated away
  7. additionhydrochloric acid was added
  8. extractionextracted with diethyl ether
  9. dry with materialdried with anhydrous magnesium sulfate
  10. customThe solvent was evaporated away
  11. customthe resulting residue was recrystallized from a mixed solvent of ethanol and water

Sources & evidence

ORD record
ord-651364f736894c24b9436e1b8a8a9c0f
Source dataset
uspto-grants-2009_06
Patent number
US07541071B2

Reaction notes

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