Reaction #1201

Reaction equation

tetradecyl glycidyl ether

ethanol

glycine

NaOH

ethanol

hydrochloride

→

title compound

Yield 30.7%

4-(2-hydroxyethylamino)-1-dodecyloxy-2-methyl-2-butanol

Yield 30.7%

Conditions

Workup

1. 1
   OtherA 300-ml two-necked flask equipped with a stirrer
2. 2
   workup.DISTILLATIONAfter ethanol was distilled off under reduced pressure, methanol and hydrochloric acid
3. 3
   workup.ADDITIONwas added to the mixture
4. 4
   ExtractionThe mixture was subjected to extraction with chloroform
5. 5
   ExtractionThe resultant extract
6. 6
   Concentrationwas concentrated under reduced pressure
7. 7
   Otherthe residue was then purified by column chromatography on silica gel

Procedure

A 300-ml two-necked flask equipped with a stirrer was charged with 7.51 g (0.1 mol) of glycine, 8.3 g (0.1 mol) of 48% NaOH and 200 ml of ethanol. While stirring the mixture at 80° C., an ethanol solution of 2.70 g (10 mmol) of tetradecyl glycidyl ether was added, and the resultant mixture was stirred for 3 hours. After ethanol was distilled off under reduced pressure, methanol and hydrochloric acid was added to the mixture to acidify it. The mixture was subjected to extraction with chloroform. The resultant extract was concentrated under reduced pressure, and the residue was then purified by column chromatography on silica gel, thereby obtaining 1.17 g (yield: 30.7%) of the title compound [(IIa-10) hydrochloride].

Source