Azobisisobutyronitrile → Ethyl(2-cyano-2-methylethyl)phosphinic acid

HRID 576009Notes

Reaction equation

HRID 576009 reaction equation
[CH2:1]([P:3]([OH:5])[OH:4])[CH3:2].[C:6](#[N:10])[C:7]([CH3:9])=[CH2:8].CC(N=NC(C#N)(C)C)(C#N)C>C(O)(=O)C>[CH2:1]([P:3]([CH2:8][CH:7]([C:6]#[N:10])[CH3:9])(=[O:5])[OH:4])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 31368MethacrylonitrileHCID 13411864Ethylphosphonous acid

Product 1

HCID 86657306Ethyl(2-cyano-2-methylethyl)phosphinic acidYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

94 g (1 mol) of ethylphosphonous acid (produced as in Example 1) and 67 g (1 mol) of methacrylonitrile are initially charged in 200 ml of glacial acetic acid in a four-neck round-bottom flask equipped with stirrer, reflux condenser, thermometer and nitrogen inlet and heated. At about 100° C., 98.4 g of a 5% solution of AIBN in glacial acetic acid are added dropwise over 1 h. Thereafter, the solvent was distilled off in vacuo to leave 117 g (80% of theory) of ethyl(2-cyano-2-methylethyl)phosphinic acid.

Workup

  1. customequipped with stirrer
  2. temperaturereflux condenser
  3. temperaturethermometer and nitrogen inlet and heated
  4. distillationThereafter, the solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-23e59dcc8a24474eb5ff856e4592fc3d
Source dataset
uspto-grants-2015_05
Patent number
US09035088B2

Reaction notes

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