Dimethyl Sulfoxide → 1-Naphthaleneacetonitrile, 3-methyl-

HRID 330522Notes

Reaction equation

HRID 330522 reaction equation
[C-:1]#[N:2].[K+].BrC[C:6]1[C:15]([CH3:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.[CH3:17]S(C)=O>O>[CH3:16][C:15]1[CH:6]=[C:7]([CH2:17][C:1]#[N:2])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 9032Potassium CyanideHCID 27530932-Bromomethyl-3-methylnaphthalene

Product 1

HCID 703577721-Naphthaleneacetonitrile, 3-methyl-Yield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

KCN (1.81 g, 27.85 mmol) was added to a solution of 2-bromomethyl-3-methylnaphthalene (5.95 g, 25.32 mmol) in 150 mL of DMSO at room temperature. The resulting mixture was stirred 1 hour, diluted with water (175 mL) and stirred another 15 minutes. The resulting precipitate was collected by filtration, washed with water and dried in vacuo to give the desired product (3.71 g g, 81%) of sufficient purity for use in the subsequent reaction.

Workup

  1. stirringstirred another 15 minutes
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-bf3cda173b29432bae3c27bf397bbc7f
Source dataset
uspto-grants-1990_01
Patent number
US04897405

Reaction notes

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