Glycerol → 2,3-Dihydroxypropyl 4-(8-cyclohexyloctylamino)benzoate

HRID 905277Notes

Reaction equation

HRID 905277 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:25][CH2:26][CH:27]([CH2:29]O)[OH:28].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([O:22][CH2:29][CH:27]([OH:28])[CH2:26][OH:25])=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 753GlycerolHCID 8000Boron trifluoride etherate2×HCID 204757724-(8-Cyclohexyloctylamino)benzoic acid

Product 1

HCID 204758122,3-Dihydroxypropyl 4-(8-cyclohexyloctylamino)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 11.8 g. of 4-(8-cyclohexyloctylamino)-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 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-6f638ebab189466b9c65f525c3214ef1
Source dataset
uspto-grants-1983_12
Patent number
US04423051

Reaction notes

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