Glycerol → 2,3-Dihydroxypropyl 4-(4-tetradecenylamino)phenylpropionate

HRID 1278298Notes

Reaction equation

HRID 1278298 reaction equation
[CH2:1]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:26])[C:23]([OH:25])=[O:24])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[OH:27][CH2:28][CH:29]([CH2:31]O)[OH:30].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[CH2:1]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:26])[C:23]([O:25][CH2:31][CH:29]([OH:30])[CH2:28][OH:27])=[O:24])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 753GlycerolHCID 8000Boron trifluoride etherate2×HCID 705588724-(4-Tetradecenylamino)phenylpropionic acid

Product 1

HCID 705596662,3-Dihydroxypropyl 4-(4-tetradecenylamino)phenylpropionate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 11.8 g. of 4-(4-tetradecenylamino)phenylpropionic acid, 1.00 g. of glycerol, and 5.35 ml. of boron trifluoride etherate in 200 ml. of toluene is stirred under reflux for 48 hours. The solution is treated with an additional 5.35 ml. of boron trifluoride etherate and refluxing is continued for 120 hours. Dilution with water and methylene chloride followed by filtration affords the product as a white solid.

Workup

  1. temperatureunder reflux for 48 hours
  2. additionThe solution is treated with an additional 5.35 ml
  3. filtrationDilution with water and methylene chloride followed by filtration

Sources & evidence

ORD record
ord-919c3915a7ba4cc4a420890e4a6659ff
Source dataset
uspto-grants-1981_07
Patent number
US04281019

Reaction notes

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