Ethylene Glycol → 2-Hydroxyethyl ethyl(2-cyanoethyl)phosphinate

HRID 1028253Notes

Reaction equation

HRID 1028253 reaction equation
[CH2:1]([P:3]([CH2:6][CH2:7][C:8]#[N:9])(=[O:5])[OH:4])[CH3:2].[CH2:10](O)[CH2:11][OH:12]>C1(C)C=CC=CC=1>[CH2:1]([P:3]([CH2:6][CH2:7][C:8]#[N:9])(=[O:4])[O:5][CH2:10][CH2:11][OH:12])[CH3:2]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 46929271Ethyl(2-cyanoethyl)phosphinic acid

Product 1

HCID 866573022-Hydroxyethyl ethyl(2-cyanoethyl)phosphinateYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

441 g (3.0 mol) of ethyl(2-cyanoethyl)phosphinic acid (produced as in Example 5) are at 85° C. dissolved in 400 ml of toluene and admixed with 248 g (4 mol) of ethylene glycol and esterified at about 100° C. in a distillation apparatus equipped with water trap during 4 h. On completion of the esterification the toluene and excess ethyl glycol is removed in vacuo to leave 510 g (89% of theory) of 2-hydroxyethyl ethyl(2-cyanoethyl)phosphinate as colorless oil.

Workup

  1. customare at 85° C.
  2. customesterified at about 100° C. in a distillation apparatus
  3. customequipped with water trap during 4 h
  4. customOn completion of the esterification the toluene and excess ethyl glycol is removed in vacuo

Sources & evidence

ORD record
ord-273e74ff8eff46d8a127eeb6954445e6
Source dataset
uspto-grants-2014_05
Patent number
US08735477B2

Reaction notes

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