Sodium Hydroxide → (2-Benzyloxyphenyl)acetic acid

HRID 1533252Notes

Reaction equation

HRID 1533252 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([O:18]CC1C=CC=CC=1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([OH:18])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 563142o-Benzyloxyphenylacetic acid, benzyl ester

Product 1

HCID 519916(2-Benzyloxyphenyl)acetic acidYield 38.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of benzyl (2-benzyloxyphenyl)acetate (100 g) in ethanol (500 ml) was added a solution of sodium hydroxide (36 g) in water (300 ml). After being stirred for 16 hours, the mixture was concentrated under reduced pressure. Water was added to the residue and the mixture was washed with diethyl ether. The aqueous layer was acidified by concentrated-hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried and evaporated in vacuo. The residual oil was crystallized from diisopropyl ether to afford (2-benzyloxyphenyl)acetic acid (28 g).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. washthe mixture was washed with diethyl ether
  4. concentrationby concentrated-hydrochloric acid solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. customdried
  8. customevaporated in vacuo
  9. customThe residual oil was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-fb3b068077864a79bc06b5914d9d2b1b
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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