Formaldehyde → Neopentyl alpha-cyanoacrylate

HRID 486178Notes

Reaction equation

HRID 486178 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:5])#[N:2].[CH2:12]=O>C1N2CCN(CC2)C1.C1(C)C=CC=CC=1>[C:1]([C:3](=[CH2:12])[C:4]([O:6][CH2:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:5])#[N:2]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 19389183Neopentyl cyanoacetate

Product 1

HCID 22266550Neopentyl alpha-cyanoacrylate

Reagents, catalysts & solvents 2

HCID 9237DabcoCatalystHCID 1140TolueneSolvent

Procedure

46.5 (0.3 mole) of neopentyl α-cyanoacetate, 8.1 g (0.27 mole) of paraformaldehyde, 140 g of toluene and 46.5 mg of triethylenediamine were reacted together under reflux and water was removed by azeotropic distillation. Then, 23.5 g of dioctyl phthalate, 0.465 g of hydroquinone and 0.93 g of phosphorus pentoxide were added and depolymerization allowed to take place at 150°-210° C. under a reduced pressure tO afford 21.65 g of crude neopentyl α-cyanoacrylate. Redistillation thereof afforded (8.3 g of neopentyl α-cyanoacrylate (b.p. 65°-67° C./2 mmHg, m.p. 40°-41° C., yield 36%).

Workup

  1. temperatureunder reflux
  2. customwater was removed by azeotropic distillation
  3. additionThen, 23.5 g of dioctyl phthalate, 0.465 g of hydroquinone and 0.93 g of phosphorus pentoxide were added
  4. customat 150°-210° C.

Sources & evidence

ORD record
ord-726a386d8cd146bd814134c103043f38
Source dataset
uspto-grants-1994_03
Patent number
US05290838

Reaction notes

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