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

HRID 1744851Notes

Reaction equation

HRID 1744851 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. Volatiles were removed under reduced pressure; 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. customVolatiles 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-e8dde596abb644eaa05bcc4fa5cc3ef5
Source dataset
uspto-grants-2006_03
Patent number
US07019006B2

Reaction notes

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