Cyclohexene → Diethyl 2-hydroxyethoxymethanephosphonate

HRID 703049Notes

Reaction equation

HRID 703049 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>[Pd].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

5

Reactant 2

HCID 8079CyclohexeneHCID 54324684Diethyl 2-(benzyloxy)ethoxymethylphosphonate

Product 1

HCID 10262588Diethyl 2-hydroxyethoxymethanephosphonate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (10%, 100 mg) was added to a solution of diethyl 2-(benzyloxy)ethoxymethylphosphonate prepared in this manner (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-31e926da4aed4c2fabc7b790fa327fa8
Source dataset
uspto-grants-1991_01
Patent number
US04981648

Reaction notes

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