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

HRID 904255Notes

Reaction equation

HRID 904255 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:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)([O:3][CH3:4])=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:42][CH2:43][CH:44](CO)[OH:45]>>[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][CH2:28][CH:44]([OH:45])[CH2:43][OH:42])=[O:26])=[CH:29][CH:30]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 3

HCID 753GlycerolHCID 6101p-Toluenesulfonic acidHCID 12898274Methyl 4-(15-carbomethoxypentadecylamino)benzoate

Product 1

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

Procedure

A mixture of 2.25 g. of methyl 4-(15-carbomethoxypentadecylamino)benzoate, 280 mg. of glycerol, and 1.37 g. of p-toluenesulfonic acid is heated at 180° C. for 4 hours and then is partitioned between ether and 3% aqueous sodium carbonate solution. The ether layer is separated, dried, and evaporated to yield 2,3-dihydroxypropyl 4-(15-carbomethoxypentadecylamino)benzoate.

Workup

  1. additionA mixture of 2.25 g
  2. customis partitioned between ether and 3% aqueous sodium carbonate solution
  3. customThe ether layer is separated
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-772d86552bef45a3a047f37d4f9c0b6c
Source dataset
uspto-grants-1980_10
Patent number
US04230628

Reaction notes

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