1-Chloromethylnaphthalene → 1-Naphthaleneacetonitrile

HRID 1421933Notes

Reaction equation

HRID 1421933 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[C-:13]#[N:14].[K+]>CN(C=O)C.[I-].[K+]>[C:3]1([CH2:2][C:13]#[N:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 68451-ChloromethylnaphthaleneHCID 9032Potassium Cyanide

Product 1

HCID 85961-NaphthaleneacetonitrileYield 98%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

1-Chloromethylnaphthalene (5.00 ml, 33 mmol) was dissolved in N,N'-dimethylformamide (50 ml) and potassium cyanide (4.31 g, 66 mmol) and potassium iodide (0.1 g) were added and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was partitioned between water (150 ml) and diethyl ether (2×100 ml). The combined organic phases were washed with water (100 ml), dried (MgSO4), filtered and concentrated in vacuo affording 5.41 g (98%) of 1-naphtylacetonitrile as an oil.

Workup

  1. customThe reaction mixture was partitioned between water (150 ml) and diethyl ether (2×100 ml)
  2. washThe combined organic phases were washed with water (100 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-143efbaba3884bab8b0f520f8e9c10f4
Source dataset
uspto-grants-2000_06
Patent number
US06080770

Reaction notes

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