Dimethylformamide → 4-(3-Methoxyphenyl)butanenitrile

HRID 2290937Notes

Reaction equation

HRID 2290937 reaction equation
S(O[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)(C1C=CC(C)=CC=1)(=O)=O.[CH3:23][N:24](C=O)C.[C-]#N.[K+]>O>[C:23]([CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)#[N:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 5904971-Tosyloxy-3-(3-methoxyphenyl)propane

Product 1

HCID 5789544-(3-Methoxyphenyl)butanenitrileYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-tosyloxy-3-(3-methoxyphenyl)propane (125 g, 0.39 mole) and DMF (400 mL) was stirred at 0° as a solution of KCN (30 g, 0.46 mole) and water (70 mL) was added dropwise. The reaction mixture was stirred at 65°-70° for 1 hour, was cooled to room temperature and poured onto ice water. The solution was extracted with ether. The extracts were washed with water, saturated aqueous NaCl, dried (MgSO4), filtered, and evaporated to yield 62 g yellow oil, (91%), M+ 175.

Workup

  1. additionwas added dropwise
  2. additionpoured onto ice water
  3. extractionThe solution was extracted with ether
  4. washThe extracts were washed with water, saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-0c94f87b0a1b4a4db100aa4fcc920555
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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