Hydrochloric Acid → 1-Oxo-2-(2-diethylphosphonoethyl)-2-methoxy-1,2-diphenylethane

HRID 2082799

Reaction equation

HRID 2082799 reaction equation
[CH3:1][O:2][CH:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].[CH:20]([P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])=[CH2:21].Cl>CS(C)=O>[O:11]=[C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:3]([CH2:21][CH2:20][P:22]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:29])([O:2][CH3:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69629Diethyl vinylphosphonateHCID 98097Methyl Benzoin

Product 1

HCID 545302481-Oxo-2-(2-diethylphosphonoethyl)-2-methoxy-1,2-diphenylethane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

16.4 g (0.1 mole) of benzoin methyl ether are dissolved in 100 ml of dimethyl sulphoxide. While passing in nitrogen, 3ml of 4 normal sodium hydroxide solution are added dropwise. Then 18 g (0.11 mole) of diethyl vinylphosphonate are added dropwise in the course of 10 minutes. The reaction mixture is stirred for 16 hours at room temperature under nitrogen and subsequently neutralised with 2 normal hydrochloric acid. After the reaction mixture has been completely concentrated under reduced pressure, the oily residue is taken up in toluene, washed twice with water and again completely concentrated by rotory evaporation to yield 1-oxo-2-(2-diethylphosphonoethyl)-2-methoxy-1,2-diphenylethane as a slightly viscous yellowish oil which crystallises on standing; m.p. 60°-62° C (initiator 1).

Workup

  1. concentrationAfter the reaction mixture has been completely concentrated under reduced pressure
  2. washwashed twice with water
  3. concentrationagain completely concentrated by rotory evaporation

Sources & evidence

ORD record
ord-12a09d2365064ae8bef93c3bfcd72764
Source dataset
uspto-grants-1978_04
Patent number
US04082821

Linked notes

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