Methane → [Hydroxy(ethyl)phosphinyl]acetic acid
Reaction equation
[CH2:1]([P:3]([CH2:6][CH2:7][O:8]CC)(=[O:5])[OH:4])[CH3:2].[OH-:11].[Na+].C>O>[CH2:1]([P:3]([OH:4])([CH2:6][C:7]([OH:8])=[O:11])=[O:5])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
16.6 g (0.1 mol) of ethyl(2-ethoxyethyl)phosphinic acid (produced as in Example 8) are dissolved in 150 ml of water and adjusted to pH 9 with 2N NaOH solution. Then, 0.45 g of charcoal with 5% Pt and 1% Bi is added, the suspension is heated to 70° C. and air is passed through the suspension at 10 l/h. All the while, the pH of the suspension is maintained at pH=9 by adding 2N NaOH solution. After the reaction is ended, the reaction solution is filtered to remove the catalyst, which is washed, and made acidic with hydrochloric acid and the water is distilled off in vacua. The residue is taken up in tetrahydrofuran and extracted. The insoluble salts are filtered off to leave 11.9 g (78% of theory) of 2-(ethylhydroxyphosphinyl)acetic acid as a colorless solid material.
Workup
- temperatureAll the while, the pH of the suspension is maintained at pH=9
- filtrationthe reaction solution is filtered
- customto remove the catalyst, which
- washis washed
- distillationthe water is distilled off in vacua
- extractionextracted
- filtrationThe insoluble salts are filtered off
Sources & evidence
- ORD record
- ord-24ca0d36aece450197c6e2efeced801f
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987489B2
Reaction notes
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