1,4-Butanediol → 4-Hydroxybutyl ethyl(2-cyanoethyl)phosphinate

HRID 576012Notes

Reaction equation

HRID 576012 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][CH2:12][CH2:13][OH:14]>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][CH2:12][CH2:13][OH:14])[CH3:2]

Participants

4

Reactant 2

HCID 80641,4-ButanediolHCID 46929271Ethyl(2-cyanoethyl)phosphinic acid

Product 1

HCID 866573014-Hydroxybutyl ethyl(2-cyanoethyl)phosphinateYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

441 g (3.0 mol) of ethyl-2-cyanoethylphosphinic acid (produced as in Example 5) are at 80° C. dissolved in 400 ml of toluene and admixed with 315 g (3.5 mol) of 1,4-butanediol 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 604 g (92% of theory) of 4-hydroxybutyl ethyl(2-cyanoethyl)phosphinate as colorless oil.

Workup

  1. customare at 80° 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-6fc92ffbb8244d1c912c80145f521777
Source dataset
uspto-grants-2015_05
Patent number
US09035088B2

Reaction notes

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