Toluene → Neopentyl alpha-cyanoacrylate

HRID 486177Notes

Reaction equation

HRID 486177 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[CH2:7](O)[C:8]([CH3:11])([CH3:10])[CH3:9].[C:13]1(C)C=CC=CC=1>S(=O)(=O)(O)O.O>[C:1]([C:3](=[CH2:13])[C:4]([O:6][CH2:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:5])#[N:2]

Participants

6

Reactant 3

HCID 1140TolueneHCID 6404Neopentyl alcoholHCID 9740Cyanoacetic acid

Product 1

HCID 22266550Neopentyl alpha-cyanoacrylateYield 94%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

51 g (0.6 mole) of cyanoacetic acid, 74 g (0.84 mole) of neopentyl alcohol, 1 g of sulfuric acid and 100 g of toluene were reacted under reflux and water produced was removed by azeotropic distillation. Thereafter, the mixture thus produced was cooled to a room temperature and filtered to remove insoluble matter. The filtrate was washed with water and dried overnight with magensium sulfate. Then, the desiccant was filtered off and the solvent was removed under a reduced pressure, followed by vacuum distillation to afford 87.1 g of neopentyl α-cyanoacrylate (b.p. 79°-81° C./3 mmHg, yield 94%).

Workup

  1. temperatureunder reflux
  2. customwas removed by azeotropic distillation
  3. customThereafter, the mixture thus produced
  4. filtrationfiltered
  5. customto remove insoluble matter
  6. washThe filtrate was washed with water
  7. dry with materialdried overnight with magensium sulfate
  8. filtrationThen, the desiccant was filtered off
  9. customthe solvent was removed under a reduced pressure
  10. distillationfollowed by vacuum distillation

Sources & evidence

ORD record
ord-f60548f332b04c4e95c794f5c522112b
Source dataset
uspto-grants-1994_03
Patent number
US05290838

Reaction notes

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