Hydrochloric Acid → HCID 19776469, compound

HRID 1612771Notes

Reaction equation

HRID 1612771 reaction equation
[CH:1]1([CH2:7][P:8](C(OCC)OCC)(=[O:12])[O:9]CC)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O>[CH:1]1([CH2:7][P:8]([OH:12])[OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19090914Ethyl diethoxymethyl(cyclohexylmethyl)phosphinate

Product 1

HCID 19776469HCID 19776469, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 38.3 g of ethyl P-cyclohexylmethyl-P-diethoxymethylphosphinate in 27 ml of water is treated with 27 ml of 37% aqueous hydrochloric acid and the mixture heated to reflux for 5 hours. The mixture is cooled to room temperature and washed with ether/hexane 1:1. Three phases are obtained. The lower 2 phases are removed and the water is removed under reduced pressure to afford cyclohexylmethylphosphonous acid as a white solid; 1H-NMR (CDCl3): δ (ppm)=7.40 (1H, broad singlet, exchanges D2O, P--OH), 7.12 (1H, d, J=526 Hz, H--P), 2.10-1.75 (7H, m, 3×CH2 +CH), 1.48-1.05 (6H, m, 3×CH3).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 5 hours
  3. washwashed with ether/hexane 1:1
  4. customThree phases are obtained
  5. customThe lower 2 phases are removed
  6. customthe water is removed under reduced pressure

Sources & evidence

ORD record
ord-80a1ebe325de4bcc8105fd33119b880a
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

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