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

HRID 1195422Notes

Reaction equation

HRID 1195422 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/0.050 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-33487f17855444e8bfb544d2a202d666
Source dataset
uspto-grants-1992_05
Patent number
US05110977

Reaction notes

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