Hydrogen Peroxide → 3-Phenoxyphenylacetamide

HRID 276148

Reaction equation

HRID 276148 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][C:15]#[N:16])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-:18].[K+].[K+].OO>CS(C)=O>[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][C:15]([NH2:16])=[O:18])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 40075m-Phenoxybenzyl cyanide

Product 1

HCID 183170403-Phenoxyphenylacetamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Phenoxyphenylacetonitrile (1.0 g; 4.8 mmol) was dissolved in DMSO (3 mL) and cooled in an ice-water bath. Potassium carbonate (0.2 g; 1.5 mmol) was added, followed by dropwise addition of 1.0 mL of 30% hydrogen peroxide. The bath was removed, and the mixture allowed to warm to room temperature while stirring for 40 min. Water was added, and the product isolated as a white crystalline solid by filtration, and washed with fresh water. mp 115-117° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. customThe bath was removed
  3. additionWater was added
  4. customthe product isolated as a white crystalline solid by filtration
  5. washwashed with fresh water

Sources & evidence

ORD record
ord-dbb83390cd10482e992f71a7aae7ee00
Source dataset
uspto-grants-2002_03
Patent number
US06353128B1

Linked notes

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