Cyclohexene → Diethyl 2-hydroxyethoxymethanephosphonate

HRID 258424Notes

Reaction equation

HRID 258424 reaction equation
C([O:8][CH2:9][CH2:10][O:11][CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])C1C=CC=CC=1.C1CCCCC=1>C(O)C>[OH:8][CH2:9][CH2:10][O:11][CH2:12][P:13](=[O:20])([O:14][CH2:15][CH3:16])[O:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 8079CyclohexeneHCID 54324684Diethyl 2-(benzyloxy)ethoxymethylphosphonate

Product 1

HCID 10262588Diethyl 2-hydroxyethoxymethanephosphonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Paladium on carbon (10%, 100 mg) was added to a solution of diethyl 2-(benzyloxy)ethoxymethylphosphonate prepared in accordance with the process of Example II above (0.9 g,2.8 mmol) and cyclohexene (2.0 ml, 20 mmol) in 20 ml ethanol under a nitrogen atmosphere. The resulting slurry was heated to reflux overnight. The catalyst was filtered off and the solution concentrated under vacuum to yield 0.5 g of diethyl 2-hydroxyethoxymethylphosphonate.

Workup

  1. temperatureThe resulting slurry was heated
  2. temperatureto reflux overnight
  3. filtrationThe catalyst was filtered off
  4. concentrationthe solution concentrated under vacuum

Sources & evidence

ORD record
ord-0db41e56e1924cd28aa83635555e87dc
Source dataset
uspto-grants-1993_11
Patent number
US05266722

Reaction notes

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