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Ethylene Glycol → 2-Hydroxyethyl ethylpropenyl-phosphinate

HRID 1621059
Notes
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Reaction equation

HRID 1621059 reaction equation
[CH2:1]([P:3]([CH:10]=[CH:11][CH3:12])(=[O:9])[O:4][CH2:5][CH2:6]CC)[CH3:2].C(O)C[OH:15]>C(O)(C([O-])=O)=O.C(O)(C([O-])=O)=O.O.O=[Ti].[K+].[K+]>[CH2:1]([P:3]([CH:10]=[CH:11][CH3:12])(=[O:9])[O:4][CH2:5][CH2:6][OH:15])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 86657322Butyl ethylpropenylphosphinate

Product 1

HCID 866573242-Hydroxyethyl ethylpropenyl-phosphinateYield 98%

Reagents, catalysts & solvents 1

HCID 91886499Dipotassium;bis(2-hydroxy-2-oxoacetate);oxotitanium;hydrateCatalyst

Conditions

Temperature
100 °C

Procedure

To 570 g (3.0 mol) of butyl ethylpropenylphosphinate (produced as in Example 6) are added 248 g (4 mol) of ethylene glycol and 0.4 g of potassium titanyl oxalate followed by stirring at 100° C. for 2 h. Volatiles are distilled off by gradual evacuation to leave 506 g (98% of theory) of 2-hydroxyethyl ethylpropenyl-phosphinate.

Workup

  1. distillationVolatiles are distilled off by gradual evacuation

Sources & evidence

ORD record
ord-21d86f61c9c941bfa118012c2672cdaa
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772519B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes