Ethanol → 2-Imidazoline, 4,4-dimethyl-1-isopropyl-2-undecyl-

HRID 1086442Notes

Reaction equation

HRID 1086442 reaction equation
[C:1](OCC)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH:17]([NH:20][CH2:21][C:22]([CH3:25])([NH2:24])[CH3:23])([CH3:19])[CH3:18].C(O)C>>[CH3:23][C:22]1([CH3:25])[CH2:21][N:20]([CH:17]([CH3:19])[CH3:18])[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:24]1

Participants

4

Reactant 3

HCID 702EthanolHCID 7800Ethyl DodecanoateHCID 795322-Amino-1,1-dimethylethylisopropylamine

Product 1

HCID 528882-Imidazoline, 4,4-dimethyl-1-isopropyl-2-undecyl-Yield 58%

Procedure

22.84 g. (100 mmoles) of ethyl dodecanoate and 15.34 g. (118 mmoles) of N1 -isopropyl-2-methyl-1,2-propanediamine was heated at 130°-230° C. until approximately 100 mmoles of ethanol was collected. Toluene was then cautiously added and the heating was continued until no more water separated. The solution was acidified, the aqueous layer was separated and basified with NaOH. This was extracted with ethyl acetate, the organic extract was dried and concentrated. The oil was distilled at 150°-152° C./1.2 mm to give 16.74 g (58%) of product.

Workup

  1. customwas collected
  2. additionToluene was then cautiously added
  3. customseparated
  4. customthe aqueous layer was separated
  5. extractionThis was extracted with ethyl acetate
  6. extractionthe organic extract
  7. customwas dried
  8. concentrationconcentrated
  9. distillationThe oil was distilled at 150°-152° C./1.2 mm

Sources & evidence

ORD record
ord-227dbcd50a9e44db9d2a48e5250c438f
Source dataset
uspto-grants-1991_07
Patent number
US05030629

Reaction notes

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