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

HRID 1028252Notes

Reaction equation

HRID 1028252 reaction equation
[CH2:1]([P:3]([CH2:6][CH:7]([C:9]#[N:10])[CH3:8])(=[O:5])[OH:4])[CH3:2].[CH2:11](O)[CH2:12][CH2:13][CH2:14][OH:15]>C1(C)C=CC=CC=1>[CH2:1]([P:3]([CH2:6][CH:7]([C:9]#[N:10])[CH3:8])(=[O:4])[O:5][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH3:2]

Participants

4

Reactant 2

HCID 80641,4-ButanediolHCID 86657306Ethyl(2-cyano-2-methylethyl)phosphinic acid

Product 1

HCID 866573084-Hydroxybutyl ethyl(2-cyano-2-methylethyl)phosphinateYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

540 g (3.0 mol) of ethyl(2-cyano-2-methylethyl)phosphinic acid (produced as in Example 6) 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. during 4 h in a distillation apparatus equipped with a water trap. After the esterification has ended, the toluene is separated off in vacuo to leave 643 g (92% of theory) of 4-hydroxybutyl ethyl(2-cyano-2-methylethyl)phosphinate as colorless oil.

Workup

  1. customare at 80° C.
  2. customequipped with a water trap
  3. customthe toluene is separated off in vacuo

Sources & evidence

ORD record
ord-1dc325450d6c4d39a2b96390db60d7c0
Source dataset
uspto-grants-2014_05
Patent number
US08735477B2

Reaction notes

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