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

HRID 878919Notes

Reaction equation

HRID 878919 reaction equation
[CH2:1]([P:3]([CH2:6][CH2:7][OH:8])(=[O:5])[OH:4])[CH3:2].[CH2:9](O)[CH2:10][CH2:11][CH2:12][OH:13]>C1(C)C=CC=CC=1>[CH2:1]([P:3]([CH2:6][CH2:7][OH:8])(=[O:4])[O:5][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH3:2]

Participants

4

Reactant 2

HCID 80641,4-ButanediolHCID 46832563HCID 46832563, compound

Product 1

HCID 468325644-Hydroxybutyl ethyl(2-hydroxyethyl)phosphinateYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

414 g (3.0 mol) of ethyl(2-hydroxyethyl)phosphinic acid (produced as in Example 7) are at 80° C. dissolved in 400 ml of toluene and admixed with 594 g (6.6 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 is removed in vacuo to leave 504 g (80% of theory) of 4-hydroxybutyl ethyl-(2-hydroxyethyl)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 is removed in vacuo

Sources & evidence

ORD record
ord-09c8d1a88b6a4a08aac37aa96134fb0e
Source dataset
uspto-grants-2015_03
Patent number
US08987490B2

Reaction notes

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