1-Butanol → Ethyl(2-ethoxyethyl)phosphinic acid

HRID 878924Notes

Reaction equation

HRID 878924 reaction equation
C(O)CCC.[OH-].[Na+].[CH2:8]([P:10]([CH2:17][CH2:18][O:19][CH2:20][CH3:21])(=[O:16])[O:11]CCCC)[CH3:9].S(=O)(=O)(O)O>O>[CH2:8]([P:10]([CH2:17][CH2:18][O:19][CH2:20][CH3:21])(=[O:11])[OH:16])[CH3:9]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 46241032Butyl ethyl(2-ethoxyethyl)phosphinate

Product 1

HCID 46235414Ethyl(2-ethoxyethyl)phosphinic acidYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

A stirred apparatus is initially charged with 150 g of butanol, 65 g of water, 150 g (3.75 mol) of sodium hydroxide and 278 g (1.25 mol) of butyl ethyl(2-ethoxyethyl)-phosphinate (produced as in Example 7). The efficiently stirred mixture is heated to about 120° C. and reacted at that temperature for about 6 hours. Then, 250 ml of water were added and the butanol was removed from the reaction mixture by distillation. Following the addition of a further 500 ml of water, the mixture is neutralized by addition of about 184 g (1.88 mol) of concentrated sulfuric acid. The water is then distilled off in vacua. The residue is taken up in tetrahydrofuran and extracted. The insoluble salts are filtered off. The solvent of the filtrate is removed in vacuo to obtain 163 g (98% of theory) of ethyl(2-ethoxyethyl)phosphinic acid as oil.

Workup

  1. customreacted at that temperature for about 6 hours
  2. customthe butanol was removed from the reaction mixture by distillation
  3. additionthe addition of a further 500 ml of water
  4. distillationThe water is then distilled off in vacua
  5. extractionextracted
  6. filtrationThe insoluble salts are filtered off
  7. customThe solvent of the filtrate is removed in vacuo

Sources & evidence

ORD record
ord-1f419d76c34f4a89983ed5acc56ce78b
Source dataset
uspto-grants-2015_03
Patent number
US08987489B2

Reaction notes

Loading…