p-Toluenesulfonic acid → 3-Hydroxypropyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate
Reaction equation
[F:1][C:2]([F:30])([F:29])[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:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1.C(O)[CH2:32][CH2:33][OH:34].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[F:1][C:2]([F:29])([F:30])[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:28]=[CH:27][C:22]([C:23]([O:25][CH2:26][CH2:32][CH2:33][OH:34])=[O:24])=[CH:21][CH:20]=1Participants
4
Procedure
A mixture of 2.25 g. of methyl 4-[15-(trifluoromethyl)pentadecylamino]benzoate, 280 mg. of 1,3-propanediol and 1.37 g. of p-toluenesulfonic acid is heated at 180° C. for 18 hours and then is partitioned between ether and 3% aqueous sodium carbonate solution. The ether layer is separated, dried, and evaporated to yield the product as a white solid.