Hydrochloric Acid → (4-Phenylbutyl)phosphonic acid

HRID 256325Notes

Reaction equation

HRID 256325 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 61.1%

Procedure

A mixture of diethyl (4-phenylbutyl)phosphonate (3.5 g, 13.0 mmole) and 6N HCl (45 ml) was refluxed under argon for 16 hours. The cooled reaction mixture was extracted with EtOAc. The organic phase was washed with saturated NaCl, dried (MgSO4), and evaporated. The crude product (2.3 g) was recrystallized from diisopropyl ether to give pure (4-phenylbutyl)phosphonic acid (1.7 g, 61%) as white needles, m.p. 92°-93° C.

Workup

  1. temperaturewas refluxed under argon for 16 hours
  2. customThe cooled reaction mixture
  3. extractionwas extracted with EtOAc
  4. washThe organic phase was washed with saturated NaCl
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product (2.3 g) was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-a50543a15f2c4dbdacade43801f2afb7
Source dataset
uspto-grants-1987_10
Patent number
US04703043

Reaction notes

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