2-Octanone → 1-Hydroxy-1-methylheptylphosphonous acid

HRID 376053Notes

Reaction equation

HRID 376053 reaction equation
[CH3:1][C:2](=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:10][P:11]=[O:12]>CO>[OH:9][C:2]([P:11]([OH:12])[OH:10])([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 80932-OctanoneHCID 22497phosphenous acid

Product 1

HCID 214699941-Hydroxy-1-methylheptylphosphonous acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of octan-2-one (3.76 g, 0.29M) and hypophosphorus acid (91.5%, 2.09 g, 0.029M) is heated at 100° C. for 12 hours in the presence of Dowex 50W x 2 ion exchange resin (1 ml, aqueous slurry). The mixture is cooled to room temperature, methanol (50 ml) is added and the Dowex is removed by filtration. The filtrate is evaporated to an oily residue, which is dissolved in ethyl acetate, washed with water, brine, then dried (MgSO4). Removal of the solvent gives 1-hydroxy-1-methylheptylphosphonous acid.

Workup

  1. customthe Dowex is removed by filtration
  2. customThe filtrate is evaporated to an oily residue, which
  3. dissolutionis dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-3033695eda954703b461a84c97d44fcc
Source dataset
uspto-grants-1996_01
Patent number
US05488171

Reaction notes

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