Malononitrile → Dihydro-2H-pyran-4,4(3H)-dicarbonitrile

HRID 982517

Reaction equation

HRID 982517 reaction equation
Cl[CH:2](Cl)[CH2:3][O:4][CH2:5][CH:6](Cl)Cl.[C:10](#[N:14])[CH2:11][C:12]#[N:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:4]1[CH2:5][CH2:6][C:11]([C:10]#[N:14])([C:12]#[N:13])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 11430Potassium CarbonateHCID 623831,1'-Oxybis(2,2-dichloroethane)

Product 1

HCID 14537194Dihydro-2H-pyran-4,4(3H)-dicarbonitrileYield 51.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 28.6 g of dichloroethyl ether, 13.2 g of malononitrile, 55.28 g of potassium carbonate and 800 ml of acetonitrile was refluxed on a steam bath for 24 hours, then filtered while hot. The filtrate was evaporated and the residue crystallized, with charcoal treatment, from 100 ml of ethanol, giving 9.5 g of tetrahydro-4H-pyran-4,4-dicarbonitrile as colorless plates, mp 110°-112° C.

Workup

  1. temperaturewas refluxed on a steam bath for 24 hours
  2. filtrationfiltered while hot
  3. customThe filtrate was evaporated
  4. customthe residue crystallized, with charcoal treatment, from 100 ml of ethanol

Sources & evidence

ORD record
ord-b7adb3f1816e4d22ba98055f4ca458c2
Source dataset
uspto-grants-1991_02
Patent number
US04996337

Linked notes

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