Water → 6-Phenylhexanenitrile

HRID 440946Notes

Reaction equation

HRID 440946 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)=O.[C-:17]#[N:18].[Na+].O>CN(C)C=O>[C:11]1([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:17]#[N:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 116301071-Methylsulfonyloxy-5-phenylpentane

Product 1

HCID 104647826-PhenylhexanenitrileYield 949.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 15.0 grams (0.0062 mole) of 1-methylsulfonyloxy-5-phenylpentane and 9.1 grams (0.190 mole) of sodium cyanide in 150 mL of N,N-dimethylformamide was heated at 50° C. to 55° C. for about 60 hours. After this time the reaction mixture was poured into 400 mL of water. The mixture was extracted with three 250 mL portions of diethyl ether. The combined extracts were then washed with three 200 mL portions of water and 200 mL of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 10.2 grams of 6-phenylhexanenitrile. The NMR spectrum was consistent with the proposed structure.

Workup

  1. extractionThe mixture was extracted with three 250 mL portions of diethyl ether
  2. washThe combined extracts were then washed with three 200 mL portions of water and 200 mL of an aqueous solution saturated with sodium chloride
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f79dbd5a05f64c40838cd993c3b0f486
Source dataset
uspto-grants-1996_05
Patent number
US05521192

Reaction notes

Loading…