Water → 4,4'-((R)-1-methylpropanedioxy)bisbenzonitrile

HRID 613792Notes

Reaction equation

HRID 613792 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[CH2:4][C@H:5]([OH:7])[CH3:6].Cl[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.O>CN(C=O)C>[CH3:6][C@@H:5]([O:7][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1)[CH2:4][CH2:3][O:8][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 121634-ChlorobenzonitrileHCID 24758Sodium hydride2×HCID 637497(-)-1,3-Butanediol

Product 1

HCID 675854964,4'-((R)-1-methylpropanedioxy)bisbenzonitrileYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (3.18 g, 133 mmol) was dispersed in 100 ml DMF and added with 1,3-(R)-butanediol (5.03 g, 55.8 mmol) while being cooled with ice. The mixture after being cooled with ice for another one hour was stirred at room temperature for 2 hours and then added with 4-chlorobenzonitrile (16.8 g, 122 mmol) at room temperature, followed by being reacted for 20 hours. After completion of the reaction, the reaction mixture was carefully added with 5 ml water to inactivate excess sodium hydride, followed by distilling out DMF in vacuum. The resulting mixture after being added with 200 ml of water was subjected to processes of extraction of an organic matter with ethyl acetate, washing with a solution of saturated sodium chloride and distillation of the solvent, followed by distillation of the oily residue thus obtained using Kugelloa distilling equipment at a temperature of 275° C. and a pressure of 0.5 mmHg thereby obtaining the intended product (13.3 g, 45.4 mmol, 81%).

Workup

  1. temperaturewhile being cooled with ice
  2. temperatureThe mixture after being cooled with ice for another one hour
  3. customby being reacted for 20 hours
  4. customAfter completion of the reaction
  5. distillationby distilling out DMF in vacuum
  6. additionThe resulting mixture after being added with 200 ml of water
  7. extractionwas subjected to processes of extraction of an organic matter with ethyl acetate
  8. washwashing with a solution of saturated sodium chloride and distillation of the solvent
  9. distillationfollowed by distillation of the oily residue
  10. customthus obtained
  11. distillationdistilling equipment at a temperature of 275° C.

Sources & evidence

ORD record
ord-8b56f25dd26b46b69a4c77123d3e6ed5
Source dataset
uspto-grants-1999_12
Patent number
US06008401

Reaction notes

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