Allyl chloride → Butyl ethylpropenylphosphinate

HRID 1621057Notes

Reaction equation

HRID 1621057 reaction equation
[CH2:1]([P:3]([O-:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2].[O-]CC.[Na+].[CH2:14](Cl)[CH:15]=[CH2:16]>C(O)C.Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([P:3]([CH:14]=[CH:15][CH3:16])(=[O:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2]

Participants

6

Reactant 3

HCID 7850Allyl chlorideHCID 2723922Sodium ethoxideHCID 86614949Butyl ethyiphosphonite

Product 1

HCID 86657322Butyl ethylpropenylphosphinateYield 66%

Reagents, catalysts & solvents 2

HCID 178418751HCID 178418751, compoundCatalystHCID 702EthanolSolvent2×

Procedure

At room temperature, a three-neck flask equipped with stirrer and high-performance condenser is initially charged with 400 g of ethanol and this initial charge is devolatilized by stirring and passing nitrogen through it. Then, under nitrogen, 3.27 g (5 mmol) of bis(triphenylphosphine)nickel dichloride and 30 g (0.2 mol) of butyl ethylphosphonite (produced as in Example 2) are added followed by the dropwise addition of initially 14.5 g (0.25 mol) of sodium ethoxide in ethanol and thereafter 19.1 g (0.25 mol) of allyl chloride. Following a reaction time of 5 hours, the reaction solution is passed for purification through a column charged with Deloxan® THP II and the solvent is removed in vacuo. The product is purified by column chromatography to obtain 25.1 g (66% of theory) of butyl ethylpropenylphosphinate as colorless oil.

Workup

  1. customAt room temperature, a three-neck flask equipped with stirrer and high-performance condenser
  2. additionthis initial charge
  3. customa reaction time of 5 hours
  4. customthe reaction solution is passed for purification through a column
  5. additioncharged with Deloxan® THP II
  6. customthe solvent is removed in vacuo
  7. customThe product is purified by column chromatography

Sources & evidence

ORD record
ord-1d54976d40bc482da6a22edf0b3ac499
Source dataset
uspto-grants-2014_07
Patent number
US08772519B2

Reaction notes

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