Tert-Butylamine → Tertiarybutylaminoethoxyethanol

HRID 978815Notes

Reaction equation

HRID 978815 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:7][CH2:8][O:9][CH:10]([OH:12])[CH3:11].[OH-].[Na+]>CO>[C:1]([NH:5][CH2:7][CH2:8][O:9][CH:10]([OH:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 14798Sodium HydroxideHCID 221454452-Chloroethoxyethanol

Product 1

HCID 86739037Tertiarybutylaminoethoxyethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 45.63 g (0.625 mole) of tertiary-butylamine and 31 g (0.25 mole) of 2-chloroethoxyethanol in 100 ml of methanol was charged to a 300 ml steel autoclave and heated under autogenous pressure for 1 hour at 150° C. The reactor was cooled and the contents removed. To the homogeneous solution was added 11 g (0.275 mole) of NaOH pellets and the reaction refluxed for 0.5-1 hour, cooled, filtered, vacuum stripped, and distilled. The yield was 31.4 g (78%).

Workup

  1. temperatureThe reactor was cooled
  2. customthe contents removed
  3. temperaturethe reaction refluxed for 0.5-1 hour
  4. temperaturecooled
  5. filtrationfiltered
  6. distillationdistilled

Sources & evidence

ORD record
ord-1903b4917735466a96b4ea299056fd61
Source dataset
uspto-grants-1987_05
Patent number
US04665234

Reaction notes

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