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1-Butanol → 3-[Ethyl(hydroxy)phosphoryl]propanoic acid

HRID 1028254
Notes
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Reaction equation

HRID 1028254 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3]C.[OH-].[Na+].[CH2:8]([P:10](CCC#N)(=[O:12])[OH:11])[CH3:9].S(=O)(=O)(O)[OH:18]>O>[CH2:8]([P:10]([OH:11])([CH2:3][CH2:2][C:1]([OH:5])=[O:18])=[O:12])[CH3:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 46929271Ethyl(2-cyanoethyl)phosphinic acid

Product 1

HCID 190110643-[Ethyl(hydroxy)phosphoryl]propanoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

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 183 g (1.25 mol) of ethyl(2-cyanoethyl)-phosphinic acid (produced as in Example 5). The efficiently stirred mixture was 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 vacuo. The residue is taken up in tetrahydrofuran and extracted. The insoluble salts are filtered off. The solvent of the filtrate is removed in vacuo and the residue is recrystallized from acetone to obtain 203 g (98% of theory) of 3-(ethylhydroxyphosphinyl)propionic acid as a solid material.

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 vacuo
  5. extractionextracted
  6. filtrationThe insoluble salts are filtered off
  7. customThe solvent of the filtrate is removed in vacuo
  8. customthe residue is recrystallized from acetone

Sources & evidence

ORD record
ord-f21ef77bed924a949c56304cce598454
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08735477B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes