Formaldehyde → N-methyl-N-tertiarybutylaminoethoxyethanol

HRID 1995769Notes

Reaction equation

HRID 1995769 reaction equation
[C:1]([NH:5][CH2:6][CH2:7][O:8][CH:9]([OH:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[CH2:12]=O>[Pd].CO>[CH3:12][N:5]([CH2:6][CH2:7][O:8][CH:9]([OH:11])[CH3:10])[C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 86739037Tertiarybutylaminoethoxyethanol

Product 1

HCID 86739036N-methyl-N-tertiarybutylaminoethoxyethanolYield 81.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A total of 145 g of tertiarybutylaminoethoxyethanol, 108 g of 37% aqueous formaldehyde, 10 g of 10% Pd/C, and 1 l of methanol were charged to an autoclave, pressured up to 1000 psi with H2 and heated at 80° C. for 8 hours. Filtration and distillation of the reaction mixture yielded 128 g of N-methyl-N-tertiarybutylaminoethoxyethanol with b.p. of 128° C. at 23 mm.

Workup

  1. filtrationFiltration and distillation of the reaction mixture

Sources & evidence

ORD record
ord-fe697eead4f6480caab9e00afd11fee4
Source dataset
uspto-grants-1983_09
Patent number
US04405811

Reaction notes

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