Potassium Hydroxide → 2-Phenylisobutyric acid

HRID 488771

Reaction equation

HRID 488771 reaction equation
C[O:2][C:3](=[O:13])[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[OH-].[K+]>CO.O>[CH3:6][C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:5])[C:3]([OH:13])=[O:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 143498Methyl 2-methyl-2-phenylpropanoate

Product 1

HCID 132222-Phenylisobutyric acidYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.10 mole (1 eq.) of α,α-dimethylphenylacetic acid methyl ester 2 in 150 mL of MeOH and 50 mL of water was added 1.02 mole (10. 1 eq.) of KOH pellets. After stirring at room temperature for 3.5 days, the methanol was stripped off by rotary evaporation. To the residual liquid was added 100 mL of water and enough concentrated HCl to bring to ˜pH 3. The aqueous solution was extracted with Et2O (3×100 mL). The combined organic layers were dried over MgSO4 and vacuum filtered. The filtrate was rotary evaporated and dried under vacuum to give a white solid as α,α-dimethylphenylacetic acid 3 (87-89%). Method D

Workup

  1. customthe methanol was stripped off by rotary evaporation
  2. additionTo the residual liquid was added 100 mL of water and enough concentrated HCl
  3. extractionThe aqueous solution was extracted with Et2O (3×100 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4 and vacuum
  5. filtrationfiltered
  6. customThe filtrate was rotary evaporated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-95ad98fa9eab4faf904f0941593e639e
Source dataset
uspto-grants-2005_12
Patent number
US06974829B2

Linked notes

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