Lauric Acid → 2,6-dimethyl-7a-undecyl-tetrahydro-2H-oxazolo[2,3-b]oxazole

HRID 2116739Notes

Reaction equation

HRID 2116739 reaction equation
[CH3:1][CH:2]([OH:9])[CH2:3][NH:4][CH2:5][CH:6]([OH:8])[CH3:7].[C:10](O)(=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>O>[CH3:1][CH:2]1[O:9][C:21]2([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10])[O:8][CH:6]([CH3:7])[CH2:5][N:4]2[CH2:3]1

Participants

4

Reactant 2

HCID 3893Lauric Acid2×HCID 8086Diisopropanolamine2×

Product 1

HCID 692034952,6-dimethyl-7a-undecyl-tetrahydro-2H-oxazolo[2,3-b]oxazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
186 °C

Procedure

To a 5 liter stirred reactor, equipped with a distillation column, condenser, and graduated receiver, the following constituents were added: 1250.0 g of diisopropanol amine (DIPA) and 1502.5 g (98%) of lauric acid. The contents were heated to 186° C. under a nitrogen blanket over a 90 minute period. During that time, 136 ml of water came overhead. The batch temperature was held at 184° C. while the pressure was dropped to 320 Pa. During the pressure reduction, 410 g of unreacted DIPA came overhead. A total of 1192 g of amide acetal derived from lauric acid was collected while the temperature was raised to 220° C. at a pressure of 280-466 Pa. This represents a 53.5% conversion of the lauric acid.

Workup

  1. customequipped with a distillation column, condenser
  2. additionthe following constituents were added
  3. customwas held at 184° C. while the pressure
  4. additionwas dropped to 320 Pa
  5. customwas collected while the temperature
  6. temperaturewas raised to 220° C. at a pressure of 280-466 Pa

Sources & evidence

ORD record
ord-00fb5ec26d9a42ca9d36a6a2cd4608c9
Source dataset
uspto-grants-2008_10
Patent number
US07439354B2

Reaction notes

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