Ethylene Glycol → HCID 86745402, compound

HRID 1090480Notes

Reaction equation

HRID 1090480 reaction equation
[C:1]([CH2:3][CH2:4][O:5][CH:6]([O:8][CH2:9][CH2:10][C:11]#[N:12])[CH3:7])#[N:2].C(#N)C=C.C(O)CO.[OH-].[Li+].COC(C)C#N.[C:29]([CH2:31][CH2:32][O:33][CH:34](O)C)#[N:30]>CO>[C:11]([CH2:10][CH2:9][O:8][CH:6]([O:5][CH2:4][CH2:3][C:1]#[N:2])[CH3:7])#[N:12].[CH3:34][O:33][CH2:32][CH2:31][C:29]#[N:30]

Participants

8

Reactant 6

HCID 174Ethylene GlycolHCID 3939Lithium HydroxideHCID 7855Acrylonitrile2×HCID 1418292-MethoxypropanenitrileHCID 13931490HCID 13931490, compound2×HCID 19915421HCID 19915421, compound

Product 1

HCID 86745402HCID 86745402, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

As in Example 1, bis(2-cyanoethoxy)ethane was prepared by the addition of 623 g (11.73 moles) of acrylonitrile to 310 g (5.0 moles) of ethylene glycol containing 1.0 g of anhydrous lithium hydroxide at 55°-60° C. over a period of 90 min. The reaction was permitted to stir an additional 2 hr at 50° C. The reaction contents were cooled to 25° C. and 88.0 g (2.75 moles) of methanol was added over a period of 1 hr while maintaining the temperature between 25°-30° C. The mixture was allowed to stir an additional 12 hr at room temperature. Analysis by NMR revealed the crude product mixture to be 79.7 wt % of bis(2-cyanoethoxy)ethane, 17.4 wt % methoxypropionitrile, 1.78 wt % methanol, 0.72 wt % of 2-cyanoethoxyethanol, and 0.33 wt % acrylonitrile.

Workup

  1. customThe reaction contents
  2. temperaturewere cooled to 25° C.
  3. temperaturewhile maintaining the temperature between 25°-30° C
  4. stirringto stir an additional 12 hr at room temperature

Sources & evidence

ORD record
ord-26b1c6a0de924aad998b2b0f5590e6c4
Source dataset
uspto-grants-1992_01
Patent number
US05081305

Reaction notes

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