Ethanol → 4-(Diethylphosphono)phenylmethanol

HRID 1683863Notes

Reaction equation

HRID 1683863 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-7a8158240ffc4593adbf09da8023bd8b
Source dataset
uspto-grants-1997_06
Patent number
US05639763

Reaction notes

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