(Aminomethyl)phosphonic acid → Glyphosate

HRID 1901391Notes

Reaction equation

HRID 1901391 reaction equation
[NH2:1][CH2:2][P:3](=[O:6])([OH:5])[OH:4].O.[C:8]([OH:12])(=[O:11])[CH:9]=O>O>[CH2:9]([NH:1][CH2:2][P:3]([OH:5])([OH:4])=[O:6])[C:8]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 14017(Aminomethyl)phosphonic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 3496GlyphosateYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aminomethylphosphonic acid (5.50 g, 0.05 mol) was dissolved in 50 ml of water maintained at 95°-100° C. Glyoxylic acid hydrate (9.70 g, 0.105 mol) was added in one portion. After 8 hours of reaction time, the water was removed on a rotary evaporator to afford a brown semisolid. Trituration of this semisolid with a small amount of water followed by filtration afforded 6.43 grams of glyphosate as a crude white solid. An additional 1.60 grams of glyphosate was recovered by chromatography of the mother liquor as described in Example 22. The total yield of crude product, which was shown by HPLC to contain 98.87 wt % glyphosate, was 8.03 grams. The actual yield of glyphosate was therefore 94.0%.

Workup

  1. temperaturemaintained at 95°-100° C
  2. customAfter 8 hours of reaction time
  3. customthe water was removed on a rotary evaporator
  4. customto afford a brown semisolid
  5. filtrationTrituration of this semisolid with a small amount of water followed by filtration

Sources & evidence

ORD record
ord-961c06540d4f42c99397cf0e795033b7
Source dataset
uspto-grants-1996_11
Patent number
US05578190

Reaction notes

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