Acetic Anhydride → Propanedinitrile, (3-methoxy-2-propenylidene)-

HRID 1657872Notes

Reaction equation

HRID 1657872 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH3:6][O:7][CH:8](OC)[CH2:9][CH:10](OC)OC.C(OC(=O)C)(=O)C>>[CH3:6][O:7][CH:8]=[CH:9][CH:10]=[C:2]([C:1]#[N:5])[C:3]#[N:4]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 8010MalononitrileHCID 66019Tetramethoxypropane

Product 1

HCID 103675Propanedinitrile, (3-methoxy-2-propenylidene)-

Procedure

A solution of 2.0 g. (31 m moles) of malononitrile and 5 g. (31 m moles) of 1,1,3,3-tetramethoxypropane in 12 ml. of acetic anhydride is heated to reflux for 24 hrs. The reaction mixture is distilled separating the lower boiling by-products and solvent from the product. The product fraction is diluted with water and the resulting precipitate is filtered and recrystallized from isopropanol-water, 1.0 g., m.p. 74°-76° C.

Workup

  1. temperatureto reflux for 24 hrs
  2. distillationThe reaction mixture is distilled
  3. customseparating the lower boiling by-products and solvent from the product
  4. additionThe product fraction is diluted with water
  5. filtrationthe resulting precipitate is filtered
  6. customrecrystallized from isopropanol-water, 1.0 g

Sources & evidence

ORD record
ord-5110e469921146e7915e91524ba04f38
Source dataset
uspto-grants-1976_06
Patent number
US03962264

Reaction notes

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