Trifluoroacetic acid → 3-(Octadecyloxy)-5-(phenylmethoxy)benzenamine
Reaction equation
CC(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[C:10]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:9]=1)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:23]([O:22][C:10]1[CH:9]=[C:8]([NH2:7])[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:11]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]Participants
4
Procedure
A solution of 28 g of 3-(octadecyloxy)-5-(phenylmethoxy)phenylcarbamic aciddimethylethyl ester and 76 ml of trifluoroacetic acid in 700 ml of methylene chloride was kept at room temperature for 2 hours. The solution was concentrated at reduced pressure and the residue was extracted with methylene chloride. The extract was washed with NaHCO3 solution, dried and concentrated to a solid which was dissolved in 1000 ml of ether.The solution was treated with 21 ml of 3N HCl in ethanol. The hydrochloridesalt which precipitated was filtered and treated with excess NaHCO3 toliberate the free base which was extracted with methylene chloride. The dried extract was concentrated at reduced pressure to give 20.4 g (89% yield, mp 57°-59°) of 3-(octadecyloxy)-5-(phenylmethoxy)benzenamine.