Water → cyclohexylmethylphosphinic acid

HRID 1612727Notes

Reaction equation

HRID 1612727 reaction equation
C(OC([P:8]([CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:12])[O:9]CC)OCC)C.O>Cl>[CH:14]1([CH2:13][PH:8](=[O:9])[OH:12])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 962WaterHCID 19090914Ethyl diethoxymethyl(cyclohexylmethyl)phosphinate

Product 1

HCID 178527044cyclohexylmethylphosphinic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 38.3 g of ethyl diethoxymethyl(cyclohexylmethyl)phosphinate in 30 ml of concentrated aqueous hydrochloric acid is treated with 30 ml of water and the mixture is heated to reflux for 5 hours. After cooling to room temperature, the mixture is washed with ether/hexane (1:1). A three-phase system is obtained. The lower phase is removed and the water removed in vacuo to give a white crystalline solid. The middle phase is an oil which crystallises on standing. These two are combined to give cyclohexylmethylphosphinic acid which is used without further purification.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 5 hours
  3. washthe mixture is washed with ether/hexane (1:1)
  4. customA three-phase system is obtained
  5. customThe lower phase is removed
  6. customthe water removed in vacuo
  7. customto give a white crystalline solid
  8. customcrystallises

Sources & evidence

ORD record
ord-950790bdf40a404a890b04df3a5e26f6
Source dataset
uspto-grants-1993_03
Patent number
US05190933

Reaction notes

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