Glycerol → 2,3-Dihydroxypropyl 4-(15-carbomethoxypentadecylamino)benzoate

HRID 1278399Notes

Reaction equation

HRID 1278399 reaction equation
[C:1]([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][CH2:18][CH2:19][NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)([O:3][CH3:4])=[O:2].[OH:30][CH2:31][CH:32]([CH2:34]O)[OH:33].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[C:1]([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][CH2:18][CH2:19][NH:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][CH2:34][CH:32]([OH:33])[CH2:31][OH:30])=[O:26])=[CH:28][CH:29]=1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 753GlycerolHCID 8000Boron trifluoride etherate2×HCID 12898273p-(15-Carbomethoxypentadecylamino)benzoic acid

Product 1

HCID 211632452,3-Dihydroxypropyl 4-(15-carbomethoxypentadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 11.8 g. of 4-(15-carbomethoxypentadecylamino)benzoic acid, 1.00 g. of glycerol, and 5.35 ml. of boron trifluoride etherate in 200 ml. of toluene is stirred under reflux for 4 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 2,3-dihydroxypropyl 4-(15-carbomethoxypentadecylamino)benzoate as a white solid.

Workup

  1. temperatureunder reflux for 4 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-1da952291e28434e813a7c258dc97036
Source dataset
uspto-grants-1981_07
Patent number
US04281018

Reaction notes

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