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Acrolein → Ethyl(2-formylethyl)phosphinic acid

HRID 1911716
Notes
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Reaction equation

HRID 1911716 reaction equation
[CH2:1]([P:3]([OH:5])[OH:4])[CH3:2].[CH:6](=[O:9])[CH:7]=[CH2:8].[O-]S(OOS([O-])(=O)=O)(=O)=O.[Na+].[Na+]>O>[CH2:1]([P:3]([CH2:8][CH2:7][CH:6]=[O:9])(=[O:5])[OH:4])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7847AcroleinHCID 62655Sodium PersulfateHCID 13411864Ethylphosphonous acid

Product 1

HCID 86657311Ethyl(2-formylethyl)phosphinic acidYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

564 g (6 mol) of ethylphosphonous acid (produced as in Example 1) are dissolved in 860 g of water and initially charged to a 5 l five-neck flask equipped with thermometer, reflux condenser, high-performance stirrer and dropping funnel. The reaction mixture is heated to 100° C. and 392 g (7 mol) of 2-propenal and 500 g of a 5% strength sodium peroxodisulfate solution (1.5 mol % based on 2-propenal) is added dropwise at atmospheric pressure over 1 h. Then, the water is distilled off in vacuo. The residue is taken up in tetrahydrofuran and the insoluble salts are filtered off. The solvent of the filtrate is removed in vacuo to leave 675 g (75% of theory) of ethyl(2-formylethyl)phosphinic acid as oil.

Workup

  1. additioninitially charged to a 5 l five-neck flask
  2. customequipped with thermometer
  3. temperaturereflux condenser, high-performance stirrer
  4. distillationThen, the water is distilled off in vacuo
  5. filtrationthe insoluble salts are filtered off
  6. customThe solvent of the filtrate is removed in vacuo

Sources & evidence

ORD record
ord-9cb24a17022f4bfdb16df32284258673
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08604108B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes