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

HRID 236846Notes

Reaction equation

HRID 236846 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[CH2:13]([O:15][CH2:16][CH2:17]Br)[CH3:14]>C(O)C>[CH3:14][CH2:13][O:15][CH2:16][CH2:17][O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 14797Potassium HydroxideHCID 611412-Bromoethyl ethyl ether

Product 1

HCID 131347364-(2-Ethoxyethoxy)benzoic acidYield 29.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 1 l three-neck flask were introduced 400 ml of 90% ethanol, 25 g of potassium hydroxide, 40 g of p-hydroxybenzoic acid and 45 g of β-ethoxyethyl bromide, and the contents were heated under reflux for 10 hours. After removing ethanol by distillation, 100 ml of a 10% aqueous solution of potassium hydroxide was added and the contents were heated under reflux for additional two hours. After acidifying with hydrochloric acid, separated acid was collected and recrystallized from benzene and then ethanol to obtain 18 g of p-(β-ethoxy)ethoxybenzoic acid. The melting point of the resulting product was 130° C.-132° C. and the elemental analysis values thereof were as follows, which accorded with the calculated values very well.

Workup

  1. temperaturethe contents were heated
  2. temperatureunder reflux for 10 hours
  3. customAfter removing ethanol
  4. distillationby distillation, 100 ml of a 10% aqueous solution of potassium hydroxide
  5. additionwas added
  6. temperaturethe contents were heated
  7. temperatureunder reflux for additional two hours
  8. customseparated acid
  9. customwas collected
  10. customrecrystallized from benzene

Sources & evidence

ORD record
ord-5958ab08cde64cc18604cfd84575d1ed
Source dataset
uspto-grants-1979_06
Patent number
US04158011

Reaction notes

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