Ethanolamine → HCID 19694659, compound

HRID 1110Notes

Reaction equation

HRID 1110 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[CH2:5]([O:19][CH2:20][CH:21]1[O:25][C:22]1([CH3:24])[CH3:23])[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]>C(O)C>[OH:2][CH2:1][CH2:3][NH:4][CH:21]([CH2:20][O:19][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])[C:22]([CH3:24])([OH:25])[CH3:23]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 196945961-Tetradecyloxy-3-methyl-2-butene oxide

Product 1

HCID 19694659HCID 19694659, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

A 100-ml two-necked flask equipped with a stirrer and a dropping funnel was charged with 15.3 g (16.7 mmol) of ethanolamine and 5.0 g of ethanol. While heating and stirring the mixture at 80° C. in a nitrogen atmosphere, an ethanol solution of 5.00 g (16.7 mmol) of 1-tetradecyloxy-3-methyl-2-butene oxide was added dropwise over 3 hours. After heating and stirring the mixture further for 16 hours, the resultant reaction mixture was concentrated under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 3.47 g (yield: 58%) of the title compound (IIc-4).

Workup

  1. customA 100-ml two-necked flask equipped with a stirrer and a dropping funnel
  2. temperatureWhile heating
  3. temperatureAfter heating
  4. stirringstirring the mixture further for 16 hours
  5. customthe resultant reaction mixture
  6. concentrationwas concentrated under reduced pressure
  7. customthe resultant residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e403979772a141b9b46f8ea7de5203df
Source dataset
uspto-grants-1998_03
Patent number
US05723497

Reaction notes

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