Sodium Hydroxide → Benzeneacetic acid, 4-(1,1-dimethylethyl)-

HRID 576057Notes

Reaction equation

HRID 576057 reaction equation
C[O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][CH:6]=1.[OH-].[Na+]>O1CCCC1.CO>[C:11]([C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:15])=[O:2])=[CH:6][CH:7]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 605629Methyl p-tert-butylphenylacetate

Product 1

HCID 118343Benzeneacetic acid, 4-(1,1-dimethylethyl)-Yield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-tert-butylphenyl acetic acid methyl ester (10.0 g, 48.5 mmol) in a mixture of tetrahydrofuran (50 mL) and methanol (50 mL) was added 6 mol/L aqueous sodium hydroxide solution (16.2 mL, 97.0 mmol), and the mixture was stirred at room temperature for 3 hr. The mixture was concentrated under reduced pressure and 6 mol/L hydrochloric acid was added thereto while cooling in ice, to adjust the pH to 4 to 5. A precipitated solid was collected by filtration to afford (4-tert-butylphenyl)acetic acid as a colorless powder (9.32 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and 6 mol/L hydrochloric acid
  2. additionwas added
  3. temperaturewhile cooling in ice
  4. filtrationA precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-9b4cfe33a62c4417adb267e56b827bf3
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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