Water → 3-(Diethylphosphono)propanoic acid

HRID 1441218Notes

Reaction equation

HRID 1441218 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][C:11]([O:13]CC1C=CC=CC=1)=[O:12])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C(OP(CCC(OCC)=O)(OCC)=O)C.O.CCCCCC>C(O)C>[CH2:7]([O:6][P:4]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 281204Ethyl 3-(diethoxyphosphoryl)propanoateHCID 71362353Benzyl 3-(diethoxyphosphoryl)propanoate

Product 1

HCID 27737363-(Diethylphosphono)propanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

40.3 mmol of benzyl 3-diethylphosphonopropionate (12.1 g) are dissolved in 100 ml of ethanol, and 2 g of catalyst (5% Pd/C) are added. After stirring under an H2 atmosphere for 4 h, the active carbon is filtered off, and the solvent is distilled out. The product results as a colourless oil which slowly solidifies to a colourless solid at room temperature. The product is slightly contaminated with ethyl 3-diethylphosphono-propionate which, where appropriate, can be transferred into the organic phase by shaking several times with water and hexane, and be removed.

Workup

  1. filtrationthe active carbon is filtered off
  2. distillationthe solvent is distilled out
  3. customThe product results as a colourless oil which
  4. customslowly solidifies to a colourless solid at room temperature
  5. custombe removed

Sources & evidence

ORD record
ord-871d39e58fe8469098a770016cdf50bc
Source dataset
uspto-grants-2010_02
Patent number
US07655624B2

Reaction notes

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