Water → HCID 13066672, compound

HRID 1163977Notes

Reaction equation

HRID 1163977 reaction equation
[C-:1]#[N:2].[K+].[CH3:4][O:5][C:6]1[C:11]([CH2:12]Br)=[CH:10][CH:9]=[CH:8][C:7]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22].O>CS(C)=O>[CH3:4][O:5][C:6]1[C:7]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])=[CH:8][CH:9]=[CH:10][C:11]=1[CH2:12][C:1]#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 130666572-Methoxyphenyl 2-methoxy-3-bromomethylphenyl ether

Product 1

HCID 13066672HCID 13066672, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Powdered Potassium cyanide (2.50 g) was added to a solution of 2-methoxyphenyl 2-methoxy-3-bromomethylphenyl ether (12.0 g) in dimethylsulfoxide (100 ml), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate and then evaporated. The resultant oily residue (9.80 g) was subjected to column chromatography on silica gel and eluted with a mixture of benzene and hexane (1:1). The eluate was evaporated to give oily 2-[2-methoxy-3-(2-methoxyphenoxy)phenyl]acetonitrile (6.20 g).

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. washeluted with a mixture of benzene and hexane (1:1)
  6. customThe eluate was evaporated

Sources & evidence

ORD record
ord-46fb3d2b31fc41158bb18777ff225c4d
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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