Acetaldehyde → 1-Benzhydrylaminoethane phosphonous acid

HRID 25982Notes

Reaction equation

HRID 25982 reaction equation
[CH:1](=O)[CH3:2].[PH2:4]([O-:6])=[O:5].[CH:7]([NH3+:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCOCC1>[CH:7]([NH:20][CH:1]([P:4]([OH:6])[OH:5])[CH3:2])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 177AcetaldehydeHCID 178527021HCID 178527021, compound

Product 1

HCID 213258901-Benzhydrylaminoethane phosphonous acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.5 Parts of freshly distilled acetaldehyde was added to a suspension of 2.5 parts of benzhydrylammonium hypophosphite in 10 parts of dioxan at room temperature and the mixture stirred for 15 minutes. The mixture was then heated slowly to 50° when solution occurred and a flocculent precipitate immediately formed. The mixture was allowed to cool to room temperature with vigorous stirring and the orange yellow solid filtered off washed with dioxan and ether and finally with a little cold ethanol to give DL-1-benzhydrylaminoethane phosphonous acid, melting point 220°-221°.

Workup

  1. temperatureThe mixture was then heated slowly to 50° when solution
  2. customa flocculent precipitate immediately formed
  3. stirringwith vigorous stirring
  4. filtrationthe orange yellow solid filtered off
  5. washwashed with dioxan and ether and finally with a little cold ethanol

Sources & evidence

ORD record
ord-c36872adac9c4d889b5e07045c57da1c
Source dataset
uspto-grants-1979_04
Patent number
US04147780

Reaction notes

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