Water → HCID 13776037, compound

HRID 845344Notes

Reaction equation

HRID 845344 reaction equation
[CH2:1]([CH:13]1[CH2:18][C:17](=O)[CH2:16][CH2:15][C:14]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:21](#[N:25])[CH2:22][C:23]#[N:24].O>NCCC(O)=O.C(Cl)(Cl)Cl>[C:23]([C:22]([C:21]#[N:25])=[C:14]1[CH2:15][CH2:16][C:17](=[C:22]([C:21]#[N:25])[C:23]#[N:24])[CH2:18][CH:13]1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])#[N:24]

Participants

6

Reactant 3

HCID 962WaterHCID 8010MalononitrileHCID 137760342-Dodecylcyclohexane-1,4-dione

Product 1

HCID 13776037HCID 13776037, compound

Reagents, catalysts & solvents 2

HCID 239Beta-AlanineCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 2 g (0.0071M) of thus obtained 2-dodecyl-1,4-cyclohexane-dione and 1.4 g (0.0212M) of malononitrile was heated in a water bath to make a solution. β-alanine as a catalyst and 2 ml of water were added to the solution and stirred at a temperature between 40° C. and 50° C. for 8 hours to react the mixture. After cooling, the reacted mixture was dissolved in chloroform, and rinsed with water and dried. The dried material was concentrated under reduced pressure, and purified through silica gel column chromatography. As a result, 1.26 g of white crystal of 1,4-bis-(dicyanomethylene)-2-dodecyl cyclohexane was obtained. The obtained compound had a melting point of 97° C. and an infrared absorption band of 2250 cm-1 which corresponds to a cyano group.

Workup

  1. temperaturewas heated in a water bath
  2. customto react the mixture
  3. temperatureAfter cooling
  4. washrinsed with water
  5. customdried
  6. concentrationThe dried material was concentrated under reduced pressure
  7. custompurified through silica gel column chromatography

Sources & evidence

ORD record
ord-e50fbc96f6d446cbbb52ea8bd566fba3
Source dataset
uspto-grants-1988_07
Patent number
US04758381

Reaction notes

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