Sodium Hydroxide → Phenylacetic Acid

HRID 354381Notes

Reaction equation

HRID 354381 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH2:18][C:19]([O:21]C)=[O:20])[CH:5]=[CH:6][C:7]=1NC(NC1C=CC=CC=1)=O.[OH-].[Na+]>C1COCC1>[C:4]1([CH2:18][C:19]([OH:21])=[O:20])[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23511986HCID 23511986, compound

Product 1

HCID 999Phenylacetic AcidYield 206.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-chloro-4-(N′-phenylureido)phenylacetate (1.79 g, 5.62 mmol) in THF (30 ml) was added 0.25 N NaOH (30 ml). After stirring at room temperature for 20 h, the solvent was concentrated in vacuo. The residue was triturated by the addition of 1 N HCl and dried at 60° C. for 2 days under a reduced pressure to give 3-chloro-4-N′-phenylureido)phenylacetic acid (1.58 g, 92%) as pale brown solid. 1H-NMR (DMSO-d6) δ3.55 (s, 2H), 6.99 (t, J=7.3 Hz, 1H), 7.17 (d, J=8.3 Hz, 1H), 7.29 (t, J=7.6 Hz, 2H), 7.36 (s, 1H), 7.46 (d, J=8.0 Hz, 2H), 8.07 (d, J=8.3 Hz, 1H), 8.28 (s, 1H), 9.37 (s, 1H), 12.37 (br, 1H).

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. customThe residue was triturated by the addition of 1 N HCl
  3. customdried at 60° C. for 2 days under a reduced pressure

Sources & evidence

ORD record
ord-5f044fd36de44bc792248d87ee7ab87c
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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