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

HRID 1294473Notes

Reaction equation

HRID 1294473 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-19a2be3ca9014f2282c12bdb03d1fdee
Source dataset
uspto-grants-2007_07
Patent number
US07241758B2

Reaction notes

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