Potassium Hydroxide → 2-Phenyl-4,6-bis[2-hydroxy-4-(11-hydroxyundecyloxy)phenyl]-1,3,5-triazine

HRID 362684Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[C:14]1([C:20]2[N:25]=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][C:27]=3[OH:33])[N:23]=[C:22]([C:34]3[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][C:35]=3[OH:41])[N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-:42].[K+]>COCCOCCOC>[C:14]1([C:20]2[N:21]=[C:22]([C:34]3[CH:39]=[CH:38][C:37]([O:40][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[CH:36][C:35]=3[OH:41])[N:23]=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:42])=[CH:28][C:27]=3[OH:33])[N:25]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Under nitrogen, 32.4 g (128 mmol) of 11-bromo-1-undecanol are added at 80° C. to a solution of 20.0 g (54 mmol) of 2-phenyl-4,6-bis(2,4-dihydroxyphenyl)-1,3,5-triazine, 6.6 g (109 mmol) of potassium hydroxide and 150 ml of diglyme. The mixture is heated at 100° C. for 14 hours and filtered while hot, and the filtrate is cooled to 0° C. The solid which crystallizes therefrom is filtered off, pressed and dried for 24 hours under reduced pressure (60 mmHg, 60° C.), giving 27.6 g (72% yield) of 2-phenyl-4,6-bis[2-hydroxy-4-(11-hydroxyundecyloxy)phenyl]-1,3,5-triazine as a pale yellow solid of melting point 126°-135° C.

Workup

filtrationfiltered while hot, and the filtrate
temperatureis cooled to 0° C
customThe solid which crystallizes
filtrationtherefrom is filtered off
customdried for 24 hours under reduced pressure (60 mmHg, 60° C.)

Sources & evidence

ORD record: ord-df18c56e739640dcb16807e959cdbdbd
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869588

Reaction notes

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