Sodium Hydroxide → (3-Benzyloxyphenyl)acetic acid

HRID 1670340Notes

Reaction equation

HRID 1670340 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]([O:18]CC2C=CC=CC=2)=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15470856Benzyl 2-(3-(benzyloxy)phenyl)acetate

Product 1

HCID 4592030(3-Benzyloxyphenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The crude benzyl 2-(3-(benzyloxy)phenyl)acetate was dissolved in a mixture of MeOH (20 mL) and THF (50 mL). To this solution was added 40 mL of 1N NaOH (40 mmol). The reaction mixture was stirred at room temperature for 2 h. The organic solvent was removed in vacuo. The remaining aqueous solution was extracted with diethyl ether (2×50 mL). The aqueous solution was then acidified with 1N HCl (50 mL) and the title compound precipitated. The solid was collected by filtration (4.35 g, 90% two steps). MS (ESI+) m/z 265 (M+Na)+.

Workup

  1. customThe organic solvent was removed in vacuo
  2. extractionThe remaining aqueous solution was extracted with diethyl ether (2×50 mL)
  3. customthe title compound precipitated
  4. filtrationThe solid was collected by filtration (4.35 g, 90% two steps)

Sources & evidence

ORD record
ord-44c29f0a61c54441bf97eca6a233f301
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

Loading…