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

HRID 277720

Reaction equation

HRID 277720 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
  3. filtrationThe resulting solids were filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-af08657aad9e4b77a676d6e70de6dc3d
Source dataset
uspto-grants-2002_03
Patent number
US06358945B1

Linked notes

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