Hydrochloric Acid → Phenylacetic Acid

HRID 554627Notes

Reaction equation

HRID 554627 reaction equation
[C:1]1([CH2:7][C:8]([O:10]C)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>C1COCC1.CO>[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7559Methyl phenylacetateHCID 14798Sodium Hydroxide2×

Product 1

HCID 999Phenylacetic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl phenylacetate (5.03 g, 33.5 mmol) was treated with 1N aqueous NaOH (22 mL, 22 mmol) in THF (40 mL) and MeOH (4 mL), and stirred overnight at room temperature. Additional 1N aqueous NaOH (22 mL, 22 mmol) was added, and the reaction was stirred for 6 hours at room temperature. The mixture was acidified with 1N aqueous HCl to pH 3-4 and extracted with EtOAc three times. The combined organic layers were dried and concentrated to give phenyl-acetic acid.

Workup

  1. stirringthe reaction was stirred for 6 hours at room temperature
  2. extractionextracted with EtOAc three times
  3. customThe combined organic layers were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c6d10ee40261447f9d27566f55635ca0
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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