Glycerol → 2,3-Dihydroxypropyl 4-(16-bromohexadecylamino)benzoate

HRID 648314Notes

Reaction equation

HRID 648314 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][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][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1.[OH:28][CH2:29][CH:30]([CH2:32]O)[OH:31].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][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][NH:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][CH2:32][CH:30]([OH:31])[CH2:29][OH:28])=[O:24])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 753GlycerolHCID 8000Boron trifluoride etherate2×HCID 204825194-(16-Bromohexadecylamino)benzoic acid

Product 1

HCID 204825222,3-Dihydroxypropyl 4-(16-bromohexadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 11.8 g. of 4-(16-bromohexadecylamino)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 48 hours. The solution is treated with an additional 5.35 ml. of boron trifluoride etherate and refluxing for 120 hours. Dilution with water and methylene chloride followed by filtration affords 2,3-dihydroxypropyl 4-(16-bromohexadecylamino)benzoate 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-f6e94b26ef8b45c0b0b96fac76be8211
Source dataset
uspto-grants-1983_10
Patent number
US04411903

Reaction notes

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