Formaldehyde → N,N-bis-hydroxymethyl-glycine
Reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[CH3:6][OH:7].[CH2:8]=[O:9]>C(N(CC)CC)C>[OH:7][CH2:6][N:1]([CH2:8][OH:9])[CH2:2][C:3]([OH:5])=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
37.5 g. of glycine are added to a hot solution of 500 ml. anhydrous methanol, 47.0 g. of triethylamine and 30.0 g. of paraformaldehyde. N,N-bis-hydroxymethyl-glycine obtained in the reaction mixture is reacted without isolation with 55.0 g. of diethyl-phosphite and the reaction mixture is boiled under stirring for 1 hour. To the obtained solution containing dialkyl-[N-(N-hydroxy-methylene-glycine)-methylene]-phosphite 210 ml. of conc. hydrochloric acid are added and the formed N-phosphonomethyl-glycine-ethyl ester is heated for 1.5 hours at 115° C. to hydrolyze it to N-phosphonomethyl-glycine. The reaction mixture is processed and thus 66-68 g. of N-phosphonomethyl-glycine are obtained in crystalline form, purity: above 96%.
Sources & evidence
- ORD record
- ord-886cde9460b74b629bc57f7219622d8b
- Source dataset
- uspto-grants-1984_12
- Patent number
- US04486359
Reaction notes
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