Ethyl Lactate → 2-hydroxy-N-octyl-propanamide

HRID 2261719Notes

Reaction equation

HRID 2261719 reaction equation
[CH2:1]([NH2:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:10](OCC)(=[O:14])[CH:11]([CH3:13])[OH:12]>>[CH2:1]([NH:9][C:10](=[O:14])[CH:11]([CH3:13])[OH:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 7344Ethyl LactateHCID 8143Octylamine

Product 1

HCID 2234322-hydroxy-N-octyl-propanamide

Conditions

Temperature
90 °C

Procedure

388 g (3 mol) of n-octylamine were added to 473 g (4 mol) of ethyl lactate in a round-bottomed flask with a distillation apparatus over the course of two hours with stirring and a nitrogen purge. When the addition was complete, the temperature was increased to 90° C. and the ethanol which formed was distilled. The temperature was then increased to 140° C. and maintained for one hour. The pressure was then reduced to 50 mbar and unreacted ethyl lactate was distilled. 585 g of octllactamide were obtained as a clear, pale pink-colored liquid. 1H-NMR (400 MHz, CDCl3): 0.8 ppm (3H), 1.2 ppm (10H), 1.4 ppm (3H), 1.5 ppm (2H), 3.2 ppm (2H), 4.0 ppm (0.8H, br), 4.2 ppm (1H), 6.8 ppm (1H).

Workup

  1. customa nitrogen purge
  2. additionWhen the addition
  3. customthe ethanol which formed
  4. distillationwas distilled
  5. temperatureThe temperature was then increased to 140° C.
  6. temperaturemaintained for one hour
  7. distillationwas distilled
  8. custom585 g of octllactamide were obtained as a clear, pale pink-colored liquid

Sources & evidence

ORD record
ord-5d43eda338144e5d96c1ea93ac814713
Source dataset
uspto-grants-2010_12
Patent number
US07847123B2

Reaction notes

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