Toluene → Neopentyl alpha-cyanoacrylate

HRID 1682244Notes

Reaction equation

HRID 1682244 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-bd2ea1e339424da48487bf58c2e0f194
Source dataset
uspto-grants-1992_12
Patent number
US05175337

Reaction notes

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