Glycidol → 3-(Octadecylamino)propane-1,2-diol

HRID 128894Notes

Reaction equation

HRID 128894 reaction equation
[CH2:1]([NH2:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:20]1[O:22][CH:21]1[CH2:23][OH:24]>CO>[CH2:1]([NH:19][CH2:20][CH:21]([OH:22])[CH2:23][OH:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 11164GlycidolHCID 15793Octadecylamine

Product 1

HCID 1200883-(Octadecylamino)propane-1,2-diolYield 95.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Octadecylamine (18 g) was dissolved in 200 ml methanol and heated to 60° C. Glycidol (4.95 g) was added dropwise under constant stirring over one and half hours. The reaction mixture was kept under reflux for one additional hour, and then cooled to room temperature, and evaporated to dryness, resulting in 22 g white solid material. This was then recrystallized from hexane, to yield ODP, mp 81°-83° C.

Workup

  1. temperatureunder reflux for one additional hour
  2. temperaturecooled to room temperature
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-f27d6f854cac411c9ea3585343c87e9f
Source dataset
uspto-grants-1995_11
Patent number
US05466438

Reaction notes

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