Water → HCID 20513451, compound

HRID 1164000Notes

Reaction equation

HRID 1164000 reaction equation
[C-:1]#[N:2].[Na+].[C:4]([O:7][C:8]1[C:13]([CH2:14]Br)=[CH:12][CH:11]=[CH:10][C:9]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])(=[O:6])[CH3:5].O>CS(C)=O>[C:4]([O:7][C:8]1[C:9]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:10][CH:11]=[CH:12][C:13]=1[CH2:14][C:1]#[N:2])(=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 20513445HCID 20513445, compound

Product 1

HCID 20513451HCID 20513451, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Powdered sodium cyanide (3.65 g) was added to a solution of 2-chlorophenyl 2-acetoxy-3-bromomethylphenyl ether (22 g) in dimethylsulfoxide (80 ml) with stirring at room temperature, and the mixture was stirred at the same temperature for 10 minutes. Water (200 ml) was added to the reaction mixture and extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate and then evaporated to give oily 2-[2-acetoxy-3-(2-chlorophenoxy)phenyl]acetonitrile (19 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 10 minutes
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-6c9ad28d23644ab8ab54f5681165ca7e
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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