Sodium Hydroxide → 3-(3-Methoxy-4-benzyloxyphenyl)propionic acid

HRID 458787Notes

Reaction equation

HRID 458787 reaction equation
C([O:8][C:9](=[O:28])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:14]([O:26][CH3:27])[CH:13]=1)C1C=CC=CC=1.[OH-].[Na+]>CO.O1CCOCC1>[CH2:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][C:9]([OH:28])=[O:8])=[CH:13][C:14]=1[O:26][CH3:27])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 693534603-(4-Benzyloxy-3-methoxy-phenyl)-propionic acid benzyl ester

Product 1

HCID 27524153-(3-Methoxy-4-benzyloxyphenyl)propionic acidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of-3-(4-benzyloxy-3-methoxy-phenyl)-propionic acid benzyl ester (11.03 g, 29.30 mmol), in MeOH (110 ml) and dioxane (145 ml), was added dropwise aqueous NaOH 2N (139 ml, 278 mmol). The resulting yellow homogeneous mixture was then stirred at 50° C. for 17 h. The reaction mixture was then concentrated in vacuo and washed with Et2O (100 ml). The aqueous phase was acidified (pH=1) with HCl 2N and extracted three times with CH2Cl2. The combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give the title carboxylic acid (8.4 g, 29.30 mmol, 100%) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. washwashed with Et2O (100 ml)
  3. extractionextracted three times with CH2Cl2
  4. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2bc885635a2e488eba8d758bfb256bfc
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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