Water → Benzeneacetic acid, 4-(1,1-dimethylethyl)-

HRID 2297740Notes

Reaction equation

HRID 2297740 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14]C)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O>CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 962WaterHCID 605629Methyl p-tert-butylphenylacetate

Product 1

HCID 118343Benzeneacetic acid, 4-(1,1-dimethylethyl)-Yield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-t-butylphenylacetate (20 mmol) was dissolved in MeOH (160 mL) and treated with water (40 mL) and LiOH monohydrate (30 mmol). The reaction was allowed to stir at room temperature overnight. The volatiles were removed under reduced pressure and the remaining residue was diluted with water and neutralized to pH 4 with 1 N sulfuric acid. The resulting solids were filtered, washed with water and dried to leave 4-t-butylphenylacetic acid as an off-white solid (3.8 g, 99%).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionthe remaining residue was diluted with water and neutralized to pH 4 with 1 N sulfuric acid
  3. filtrationThe resulting solids were filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-72e0cdf613c74c739d1b5e08b2470c1b
Source dataset
uspto-grants-2002_12
Patent number
US06492393B1

Reaction notes

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