Sodium Hydroxide → 1-Oxo-2-ethoxy-2-(2-ethylphosphonoethyl)-1,2-diphenylethane

HRID 2372873

Reaction equation

HRID 2372873 reaction equation
[O:1]=[C:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:3]([O:20][CH2:21][CH3:22])([CH2:10][CH2:11][P:12]([O:17]CC)([O:14][CH2:15][CH3:16])=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OC(C1C=CC=CC=1)C(=O)C1C=CC=CC=1)C.CCOP(OC=C)(OCC)=O.[OH-].[Na+]>C(O)C>[O:1]=[C:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:3]([O:20][CH2:21][CH3:22])([CH2:10][CH2:11][P:12]([OH:17])([O:14][CH2:15][CH3:16])=[O:13])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 101778Benzoin ethyl etherHCID 573017Diethyl vinyl phosphateHCID 539682701-Oxo-2-ethoxy-2-(2-diethylphosphonoethyl)-1,2-diphenylethane

Product 1

HCID 539050581-Oxo-2-ethoxy-2-(2-ethylphosphonoethyl)-1,2-diphenylethane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Oxo-2-ethoxy-2-(2-diethylphosphonoethyl)-1,2-diphenylethane (25 g, prepared from benzoin ethyl ether and diethyl vinyl phosphonate as described in Example 3 of U.S. Pat. No. 4,082,821) is dissolved in ethanol (200 ml). Sodium hydroxide (20 g) is added to the solution and the mixture is heated under reflux for 3 hours. The ethanol is removed by rotary evaporation, water is added, and the mixture is washed with diethyl ether (4×100 ml) to remove unreacted starting material. Concentrated hydrochloric acid is added to the aqueous mixture until the pH is zero. The resulting mixture is washed with ether, water is evaporated and the residue is recrystallised from a mixture of acetone and ether to give 12.5 g of product, a compound of formula XVIII where R1 is ethoxy, R3 and Ar1 are each phenyl, R7 is --CH2CH2 -- and R8 is --CH2CH3.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. customThe ethanol is removed by rotary evaporation, water
  4. additionis added
  5. washthe mixture is washed with diethyl ether (4×100 ml)
  6. customto remove unreacted
  7. additionConcentrated hydrochloric acid is added to the aqueous mixture until the pH is zero
  8. washThe resulting mixture is washed with ether, water
  9. customis evaporated
  10. customthe residue is recrystallised from a mixture of acetone and ether

Sources & evidence

ORD record
ord-5ffa2cc03e754866a4fc310df225cf4b
Source dataset
uspto-grants-1992_03
Patent number
US05100987

Linked notes

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