Hydrochloric Acid → 1,12-Bis(3,4-dicyanophenoxy) dodecane

HRID 903118

Reaction equation

HRID 903118 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[N+]([C:18]1[CH:19]=[C:20]([C:26]#[N:27])[C:21](=[CH:24][CH:25]=1)[C:22]#[N:23])([O-])=O.[C:28](=[O:31])([O-])[O-].[K+].[K+].Cl>CS(C)=O>[C:26]([C:20]1[CH:19]=[C:18]([CH:25]=[CH:24][C:21]=1[C:22]#[N:23])[O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][O:31][C:28]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([C:26]#[N:27])[CH:19]=1)#[N:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium Carbonate2×HCID 797581,12-DodecanediolHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 125786551,12-Bis(3,4-dicyanophenoxy) dodecane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1,12-dodecanediol (20.4 g, 0.10 mol), 4-nitrophthalonitrile (35 g, 0.20 mol), anhydrous potassium carbonate (69 g, 0.50 mol) and 180 ml of dimethyl sulfoxide was heated at 70°-75° C. for 6 hours under a nitrogen atmosphere. The potassium carbonate was added in three portions. After cooling, the content was slowly poured into 500 ml of cold dilute (2 N) hydrochloric acid. The aqueous solution was extracted with four, 100 ml portions of chloroform. The combined extract was washed several times with water, charcoaled, dried over anhydrous sodium sulfate and concentrated to afford 42 g of crude product. Recrystallization from ethanol-water yielded 24.4 g (54%), m.p. 104°-107° C. of 1,12-bis(3,4-dicyanophenoxy) dodecane.

Workup

  1. temperaturewas heated at 70°-75° C. for 6 hours under a nitrogen atmosphere
  2. temperatureAfter cooling
  3. additionthe content was slowly poured into 500 ml
  4. extractionThe aqueous solution was extracted with four, 100 ml portions of chloroform
  5. extractionThe combined extract
  6. washwas washed several times with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto afford 42 g of crude product
  10. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-a96b19dd6bc84d4b885cea11d2a42883
Source dataset
uspto-grants-1980_10
Patent number
US04226801

Linked notes

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