Ethanol → 4-(Diethylphosphono)phenylmethanol

HRID 866083Notes

Reaction equation

HRID 866083 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([P:12]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=1)(=O)C.[OH-].[Na+].C(O)C.C(OCC)(=O)C>O1CCCC1.O>[CH2:18]([O:17][P:12]([C:9]1[CH:8]=[CH:7][C:6]([CH2:5][OH:4])=[CH:11][CH:10]=1)([O:14][CH2:15][CH3:16])=[O:13])[CH3:19]

Participants

7

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 190409274-(Diethylphosphono)phenylmethyl acetate

Product 1

HCID 190409204-(Diethylphosphono)phenylmethanolYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3.0 grams (0.01 mole) of 4-(diethylphosphono)phenylmethyl acetate in 10 mL of tetrahydrofuran was added a solution of 0.4 gram (0.01 mole) of sodium hydroxide in 1 mL of water. Upon completion of the addition, the reaction mixture was stirred at ambient temperature for one hour. After this time 5 mL of ethanol was added, and the reaction mixture was warmed to reflux, where it stirred for one hour. The reaction mixture was poured into a stirred mixture of water and ethyl acetate. The organic layer was separated and dried with magnesium sulfate. The mixture was filtered and the filtrate was concentrated under reduced pressure, yielding 2.1 grams of 4-(diethylphosphono)phenylmethanol. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe reaction mixture was warmed
  3. temperatureto reflux
  4. stirringwhere it stirred for one hour
  5. customThe organic layer was separated
  6. dry with materialdried with magnesium sulfate
  7. filtrationThe mixture was filtered
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7216560e5e4d43459d3b85d3c161f7e0
Source dataset
uspto-grants-1996_10
Patent number
US05569664

Reaction notes

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