Lauric Acid → 2-Oxazoline, 4,4-dimethyl-2-undecyl-

HRID 2352196Notes

Reaction equation

HRID 2352196 reaction equation
[C:1]([OH:14])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH2:15][C:16]([CH3:20])([CH3:19])[CH2:17]O.[OH-].[K+]>>[CH3:17][C:16]1([CH3:20])[CH2:19][O:14][C:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[N:15]1

Participants

4

Reactant 3

HCID 3893Lauric AcidHCID 118072-Amino-2-methyl-1-propanolHCID 14797Potassium Hydroxide

Product 1

HCID 951032-Oxazoline, 4,4-dimethyl-2-undecyl-Yield 87%

Procedure

64 g (320 mmoles) of dodecanoic acid and 61.1 ml (640 mmoles) of 2-amino-2-methylpropanol was placed in a two neck flask equipped with a vigreux column, distillation condenser and a thermometer. The temperature of the reaction mixture was slowly brought to 180° C. and maintained there for 9 hours. After cooling, a 10% alcoholic KOH solution (2 g, 3.6 mmoles) was added and the reflux was continued at 180° C. for 4 hours. The excess 2-amino-2-methylpropanol was distilled at aspirator pressure (86°C./ 18 mm). When the vapor temperature reached 103° C., the distillation was discontinued and the residue was taken in petroleum ether and filtered. The filtrate was washed with dilute KOH, water, dried and concentrated. The oil was distilled at 120° C./ 1.2 mmHg to give 70.5 g (87%) of product.

Workup

  1. customequipped with a vigreux column, distillation condenser
  2. customwas slowly brought to 180° C.
  3. temperaturemaintained there for 9 hours
  4. temperatureAfter cooling
  5. distillationThe excess 2-amino-2-methylpropanol was distilled at aspirator pressure (86°C./ 18 mm)
  6. customreached 103° C.
  7. distillationthe distillation
  8. filtrationfiltered
  9. washThe filtrate was washed with dilute KOH, water
  10. customdried
  11. concentrationconcentrated
  12. distillationThe oil was distilled at 120° C./ 1.2 mmHg

Sources & evidence

ORD record
ord-4376693b40264a47bd5f2576cdd4bf98
Source dataset
uspto-grants-1989_10
Patent number
US04876249

Reaction notes

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