1,4-Butanediol → 4-Hydroxybutyl 3-(ethyl-4-hydroxybutoxyphosphinyl)-2-methylpropionate

HRID 1028259Notes

Reaction equation

HRID 1028259 reaction equation
[CH2:1]([P:3]([OH:11])([CH2:5][CH:6]([CH3:10])[C:7]([OH:9])=[O:8])=[O:4])[CH3:2].[CH2:12](O)[CH2:13][CH2:14][CH2:15][OH:16]>C1(C)C=CC=CC=1>[CH2:1]([P:3]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])([CH2:5][CH:6]([CH3:10])[C:7]([O:9][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])=[O:8])=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 80641,4-ButanediolHCID 462165003-(Ethylhydroxyphosphinyl)-2-methylpropionic acid

Product 1

HCID 866573094-Hydroxybutyl 3-(ethyl-4-hydroxybutoxyphosphinyl)-2-methylpropionateYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

540 g (3.0 mol) of 3-(ethylhydroxyphosphinyl)-2-methylpropionic acid (produced as in Example 17) 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 894 g (92% of theory) of 4-hydroxybutyl 3-(ethyl-4-hydroxybutoxyphosphinyl)-2-methylpropionate 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-bcee0e373d8d4d26a84da10a93dc0b7d
Source dataset
uspto-grants-2014_05
Patent number
US08735477B2

Reaction notes

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