Ethylene Glycol → (2-Ethyl-[1,3]dioxolan-2-yl)-acetonitrile

HRID 1182114Notes

Reaction equation

HRID 1182114 reaction equation
[O:1]=[C:2]([CH2:6][CH3:7])[CH2:3][C:4]#[N:5].[CH2:8](O)[CH2:9][OH:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:6]([C:2]1([CH2:3][C:4]#[N:5])[O:10][CH2:9][CH2:8][O:1]1)[CH3:7]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 99203693-oxopentanenitrile

Product 1

HCID 69357458(2-Ethyl-[1,3]dioxolan-2-yl)-acetonitrile

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-oxo-pentanenitrile (1.582 g, 16.49 mmol), ethylene glycol (1.026 ml, 84.59 mmol) and a catalytic amount of p-Toluene Sulphonic acid (8 mg) in Toluene (10 ml) is refluxed at 150° C. for 2 days using Dean-Stark apparatus. The reaction mixture is diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase is dried over MgSO4, filtered, and the solvent evaporated to yield (2-ethyl-[1,3]dioxolan-2-yl)-acetonitrile. 1H NMR (400 MHz, CDCl3) d 4.15(2H,m), 4.05 (2H, m), 2.65 (2H, s), 1.80 (2H, q), 0.95 (3H, t)

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-2a163798fe114771b0fd8b5b19b1ff9a
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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