Sodium Hydroxide → 2-(3-Methoxyphenyl)-2-methylpropanoic acid

HRID 852569Notes

Reaction equation

HRID 852569 reaction equation
C([O:3][C:4](=[O:16])[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)([CH3:7])[CH3:6])C.[OH-].[Na+]>CCO>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:16])=[O:3])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10609062Ethyl 2-(3-methoxyphenyl)-2-methylpropanoate

Product 1

HCID 108216342-(3-Methoxyphenyl)-2-methylpropanoic acidYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-(3-methoxy-phenyl)-2-methyl-propionic acid ethyl ester (D98) (20.95 g, 94 mmol, 1 equiv) in EtOH (200 ml) was added 2N NaOH aqueous solution (90 ml, 180 mmol, 1.9 equiv) and the resulting mixture was stirred at 70° C. for 16 h then cooled to room temperature. Most of EtOH was removed in vacuo and the residue extracted with AcOEt then acidified to pH 1. The aqueous phase was then extracted with AcOEt and the organic phase dried over MgSO4 and concentrated in vacuo to give 2-(3-methoxy-phenyl)-2-methyl-propionic acid (D99) (15 g, 82%) as a yellow oil.

Workup

  1. temperaturethen cooled to room temperature
  2. customMost of EtOH was removed in vacuo
  3. extractionthe residue extracted with AcOEt
  4. extractionThe aqueous phase was then extracted with AcOEt
  5. dry with materialthe organic phase dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eb519b53508448378cf99a01049427f3
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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