Formaldehyde → Hydroxyethyl methyltolylamine

HRID 1835901Notes

Reaction equation

HRID 1835901 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1.[H][H].[CH2:14]=O>[Pd].O>[CH3:14][N:4]([CH2:3][CH2:2][OH:1])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 2200082-p-Tolylamino-ethanolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 76094Hydroxyethyl methyltolylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

N-(2-hydroxyethyl)-p-toluidine, 50 g, was combined with 1 g 5% palladium on carbon catalyst and charged to a pressure reactor. The pressure reactor was heated to 120° C. and fed hydrogen gas to maintain 120 psig pressure. Formaldehyde, 178 g 37% solution in water, was fed to the pressure reactor over 10 hours. After hydrogen uptake ceased, the reaction mass was filtered to remove catalyst and decanted to separate the aqueous phase.

Workup

  1. additioncharged to a pressure reactor
  2. temperatureto maintain 120 psig pressure
  3. filtrationthe reaction mass was filtered
  4. customto remove catalyst
  5. customdecanted
  6. customto separate the aqueous phase

Sources & evidence

ORD record
ord-63cdedb8f8264a4daffc54fbe30d9c76
Source dataset
uspto-grants-2004_08
Patent number
US06774193B2

Reaction notes

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