Sodium Hydroxide → 1,12-Bis(3,4-dicyanophenoxy) dodecane

HRID 903119

Reaction equation

HRID 903119 reaction equation
[CH2:1]([OH:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[OH-].[Na+].[N+]([C:20]1[CH:21]=[C:22]([C:28]#[N:29])[C:23](=[CH:26][CH:27]=1)[C:24]#[N:25])([O-])=O.[Na][Na]>O.C1C=CC=CC=1.CS(C)=O>[C:24]([C:23]1[CH:26]=[C:27]([CH:20]=[CH:21][C:22]=1[C:28]#[N:29])[O:14][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([C:28]#[N:29])[CH:21]=1)#[N:25]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 797581,12-Dodecanediol2×HCID 974431,2-Benzenedicarbonitrile, 4-nitro-HCID 141233Disodium

Product 1

HCID 125786551,12-Bis(3,4-dicyanophenoxy) dodecaneYield 45%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
140 °C

Procedure

A mixture of 1,12-dodecanediol (10.2 g, 0.051 mol), sodium hydroxide (4.6 g, 0.11 mol), 120 ml of dimethyl sulfoxide, 20 ml of benzene and 6 ml of water was stirred at reflux under a nitrogen atmosphere for 12 hours. The water was azeotroped from the mixture with a Dean-Stark trap. After cooling, 17.5 g (0.11 mol) of 4-nitrophthalonitrile was added to the disodium salt of 1,12-dodecanediol prepared above. The resulting mixture was slowly heated to 140° C. and stirred at this temperature for 8 hours. The cooled reaction mixture was poured into 400 ml of cold water. The aqueous solution was extracted with three, 75 ml portions of methylene chloride. The combined extract was washed with water, charcoaled, and dried over anhydrous sodium sulfate and concentrated at reduced pressure. Recrystallization from ethanol-water yielded 10.1 g (45%) of 1,12-bis(3,4-dicyanophenoxy) dodecane.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 12 hours
  2. customThe water was azeotroped from the mixture with a Dean-Stark trap
  3. temperatureAfter cooling
  4. customprepared above
  5. stirringstirred at this temperature for 8 hours
  6. customThe cooled reaction mixture
  7. extractionThe aqueous solution was extracted with three, 75 ml portions of methylene chloride
  8. extractionThe combined extract
  9. washwas washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated at reduced pressure
  12. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-48a60688d818483f8864702b8d2fbadb
Source dataset
uspto-grants-1980_10
Patent number
US04226801

Linked notes

Loading…