Sodium Hydroxide → [3,5-Bis(benzyloxy)phenyl]acetic acid

HRID 2253732Notes

Reaction equation

HRID 2253732 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][C:24]([O:26]CC)=[O:25])[CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][C:24]([OH:26])=[O:25])[CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 563149Ethyl 3,5-dibenzyloxyphenylacetate

Product 1

HCID 640123[3,5-Bis(benzyloxy)phenyl]acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3,5-dibenzyloxyphenylacetate (4.1 g, 10.9 mmol) in 50 ml of EtOH is added 21 ml (6 eq) of 1N NaOH. The reaction is stirred at room temperature for 2 hours at which time it is extracted with Et2O and H2O. The H2O layer is acidified to pH~1 using 1N HCl and extracted with Et2O. The organics are dried (MgSO4) and concentrated in vacuo to obtain 3,5-dibenzyloxyphenylacetic acid which is confirmed by NMR and used directly in the next step.

Workup

  1. extractionis extracted with Et2O and H2O
  2. extractionextracted with Et2O
  3. dry with materialThe organics are dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b34bed48f10849e1bc4837568714a71c
Source dataset
uspto-grants-1993_08
Patent number
US05232948

Reaction notes

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