2-(Dimethylamino)ethanol → 2-(Dimethylamino)ethyl myristate

HRID 1613690Notes

Reaction equation

HRID 1613690 reaction equation
[C:1]([OH:16])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20]O>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[C:1]([O:16][CH2:20][CH2:19][N:18]([CH3:22])[CH3:17])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 11005Myristic Acid

Product 1

HCID 966452-(Dimethylamino)ethyl myristateYield 62.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 91.35 g (0.40 mol) of myristic acid, 35.7 g (0.40 mol) of 2-dimethylaminoethanol, 0.5 g of p-toluenesulfonic acid and a suitable volume of toluene was heated at reflux for approximately 48 hours in a 1-neck 3 liter flask equipped with Dean-Stark trap and condenser. At the end of this time, 7.0 ml of water had collected in the trap. The solution was cooled, stirred with K2CO3, filtered and concentrated. The residue was distilled to give 75.0 g of product; bp=145°-50° C./0.50 mm.

Workup

  1. temperatureat reflux for approximately 48 hours in a 1-neck 3 liter flask
  2. customequipped with Dean-Stark trap and condenser
  3. customAt the end of this time, 7.0 ml of water had collected in the trap
  4. temperatureThe solution was cooled
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-a82bb315c9304b20af171b45d82b113b
Source dataset
uspto-grants-1993_03
Patent number
US05194472

Reaction notes

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