Potassium Hydroxide → 4-(Benzyloxy)benzoic acid

HRID 6586

Reaction equation

HRID 6586 reaction equation
[OH-].[K+].[CH2:3]([O:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:20][CH:21]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 191414Ethyl 4-(phenylmethoxy)benzoate

Product 1

HCID 738804-(Benzyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 0.5 g KOH in 40 ml MeOH, was added 6.5 mmol of ethyl 4-benzyloxybenzoate. After the resulting mixture was refluxed for 4 hrs, the excess methanol was removed. The residue was mixed with 30 ml water and extracted with ether twice. The water solution was acidified with conc. HCl and extracted with ethyl acetate. The ethyl acetate solution was washed with brine and dried. After evaporation of solvent, pure product was obtained in quantitative yield.

Workup

  1. temperatureAfter the resulting mixture was refluxed for 4 hrs
  2. customthe excess methanol was removed
  3. additionThe residue was mixed with 30 ml water
  4. extractionextracted with ether twice
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate solution was washed with brine
  7. customdried
  8. customAfter evaporation of solvent
  9. custompure product was obtained in quantitative yield

Sources & evidence

ORD record
ord-e893d8e4b615491698f2580374c37cef
Source dataset
uspto-grants-2006_08
Patent number
US07083832B2

Linked notes

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