4-Hydroxybenzoic Acid → 4-(2-Methoxyethoxy)benzoic acid

HRID 747072Notes

Reaction equation

HRID 747072 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:14][CH2:15][O:16][CH3:17].[I-].[K+]>C(O)C.O>[CH3:17][O:16][CH2:15][CH2:14][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 809722-Bromoethyl methyl ether

Product 1

HCID 64855624-(2-Methoxyethoxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Hydroxybenzoic acid (3.00 g, 2.17×10−2 mol) was dissolved in a mixture of ethanol (15 cm3) and potassium hydroxide (3.22 g, 5.64×10−2 mol) in water (5 cm3). The solution was then heated gently and stirred before 1-bromo-2-methoxyethane (3.32 g, 2.39×10−2mol) and potassium iodide (0.01 g, 6.02×10−5 mol) was added slowly. The resulting reaction mixture was then refluxed (15 hrs) and the solvent evaporated and the resulting solid residue dissolved in water (50 cm3). The solution was washed with ether and then made strongly acidic with hydrochloric acid. The resulting precipitate was isolated and recrystallised from ethanol. Yield 1.36 g (32%).

Workup

  1. temperatureThe solution was then heated gently
  2. additionwas added slowly
  3. customThe resulting reaction mixture
  4. temperaturewas then refluxed (15 hrs)
  5. customthe solvent evaporated
  6. dissolutionthe resulting solid residue dissolved in water (50 cm3)
  7. washThe solution was washed with ether
  8. customThe resulting precipitate was isolated
  9. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-fe6df5d115ad42ccb41a9a6a14290128
Source dataset
uspto-grants-2008_07
Patent number
US07396487B2

Reaction notes

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