Hydrochloric Acid → (4-Phenylbutyl)phosphonic acid

HRID 2286837Notes

Reaction equation

HRID 2286837 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][P:11](=[O:18])([O:15]CC)[O:12]CC)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][P:11](=[O:12])([OH:18])[OH:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 13102400Diethyl 4-phenylbutylphosphonate

Product 1

HCID 13687984(4-Phenylbutyl)phosphonic acidYield 40%

Procedure

A mixture of 5.4 g (20 mmol) of diethyl 4-phenylbutylphosphonate (Compound 11, synthesized exactly by the same method described in Example 5) and 14 g of 37% hydrochloric acid was refluxed for five hours. The excess of acid was removed under vacuum leaving an oil that slowly solidified Recrystallization from an ethanol:petroleum ether (40:60) mixture gave 1.7 g (8 mmol) of white crystals.

Workup

  1. customsynthesized exactly by the same method
  2. temperaturewas refluxed for five hours
  3. customThe excess of acid was removed under vacuum
  4. customleaving
  5. customan oil that slowly solidified Recrystallization from an ethanol:petroleum ether (40:60) mixture

Sources & evidence

ORD record
ord-aa8e9f91764d4884bcadb209101958e0
Source dataset
uspto-grants-1981_05
Patent number
US04268507

Reaction notes

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