Ethanol → N,N-bis-hydroxymethyl-glycine

HRID 1153706Notes

Reaction equation

HRID 1153706 reaction equation
[CH2:1]([OH:3])C.[CH2:4]=[O:5].[NH2:6][CH2:7][C:8]([OH:10])=[O:9]>C(N(CC)CC)C>[OH:5][CH2:4][N:6]([CH2:1][OH:3])[CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 702EthanolHCID 712FormaldehydeHCID 750Glycine

Product 1

HCID 10171246N,N-bis-hydroxymethyl-glycine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 500 ml. of anhydrous ethanol, 48.0 g. of triethylamine, 30.6 g. of paraformaldehyde are added. The mixture is stirred at boiling temperature and 37.5 g. of glycine are added. N,N-bis-hydroxymethyl-glycine formed in the reaction mixture is reacted without isolation with 69.0 g. of diethyl phosphite and the reaction mixture is stirred for 20 minutes at 80° C. The reaction mixture is further processed as disclosed in Example 1. 60-62 g. of crystalline N-phosphonomethyl-glycine are obtained. Purity: above 98%.

Sources & evidence

ORD record
ord-c1248df7a29048fd87a1449d16f40191
Source dataset
uspto-grants-1984_12
Patent number
US04486359

Reaction notes

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