Water → 2-(4-Methoxyphenyl)propanenitrile

HRID 481494Notes

Reaction equation

HRID 481494 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[Li][CH3:13].CI.O>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]#[N:11])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 66031Benzeneacetonitrile, 4-methoxy-HCID 178418348HCID 178418348, compound

Product 1

HCID 122976702-(4-Methoxyphenyl)propanenitrileYield 112.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-methoxyphenylacetonitrile (17 g, 0.11 mol) and MeLi (1M; 100 ml, 0.11 mol) in THF (200 ml) was added MeI (32 g, 0.22 mol) at -78° C. After the mixture was stirred for 3 hours, the mixture was poured into H2O (100 ml), and extracted with AcOEt. The combined extracts were dried (Na2SO4), and concentrated to give a yellow oil (20 g), which was purified by a column chromatography on silica gel to give Compound 13 as a colorless oil (11 g, 62%).

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-afab7ebbb6f14c16a09c8ff51dc36f54
Source dataset
uspto-grants-1998_08
Patent number
US05789423

Reaction notes

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