Butyl glycidyl ether → 2,4-Di[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-6-methoxy-1,3,5-triazine

HRID 2379669Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[OH:22])[N:12]=[C:11]([O:23][CH3:24])[N:10]=1.[CH2:25]([O:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:26]1[O:28][CH2:27]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:27][CH:26]([OH:28])[CH2:25][O:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:27][CH:26]([OH:28])[CH2:25][O:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:17][C:16]=2[OH:22])[N:12]=[C:11]([O:23][CH3:24])[N:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

10 g of 2,4-di(2,4-dihydroxyphenyl)-6-methoxy-1,3,5-triazine are stirred for 3 hours at 130° C. with 100 ml of butyl glycidyl ether and 0.20 g of tetrabutylammonium bromide. The mixture is subsequently allowed to cool to 80° C., 100 ml of ethyl acetate and 2.0 g of Prolith Rapid are added, the mixture is filtered through kieselguhr, and the solvent is removed under reduced pressure. The excess butyl glycidyl ether is then removed by vacuum distillation, giving 2,4-di[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-6-methoxy-1,3,5-triazine, which, after recrystallisation from ethanol, has a melting point of 108°-109° C.

Workup

filtrationthe mixture is filtered through kieselguhr
customthe solvent is removed under reduced pressure
customThe excess butyl glycidyl ether is then removed by vacuum distillation

Sources & evidence

ORD record: ord-dc03bcce5d5444c28a4653e4995b70ac
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05364749

Reaction notes

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