Water → HCID 136386385, compound

HRID 634963Notes

Reaction equation

HRID 634963 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]=2O)[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=2[OH:30])[N:10]=1.[C:31](=[O:34])([O-])[O-].[K+].[K+].Br[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].O>C(OCC)C>[OH:30][C:24]1[CH:25]=[C:26]([O:29][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:27]=[CH:28][C:23]=1[C:11]1[N:10]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([O:8][CH2:19][CH2:20][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:7][C:2]=2[OH:1])[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:5][CH2:4][CH2:3][CH2:2][CH2:7][CH3:6])=[CH:17][C:16]=2[O:34][CH2:31][CH2:25][CH2:24][CH2:23][CH2:28][CH3:27])[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 1357148802,4,6-tris(2,4-dihydroxyphenyl)-1,3,5-triazine

Product 1

HCID 136386385HCID 136386385, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

Under nitrogen, a mixture of 60.8 g (0.150 mol) of 2,4,6-tris(2′,4′-dihydroxyphenyl)-1,3,5-triazine and 87.1 g (0.630 mol) of potassium carbonate in 700 ml of 2-ethoxyethane (Fluka, 99.5%) is added dropwise over the course of 15 minutes to 134.8 (0.800 mol) of 1-bromohexane (Fluka, 98%) which is held at 80° C. The mixture is subsequently heated at 120° C. for 20 h. After cooling, the reaction mixture is poured into 8 l of cold water. After 24 hours at 25° C. the precipitate is filtered off, washed with water (300 ml) and dried. The crude product is chromographed [2.5 kg of silica gel 60 (230-400 mesh), Ø=13 cm; h=60 cm; eluted with hexane/ethyl acetate (39:1)]. Removal of the solvent from the main fraction gives 69.2 g of 2,4-bis(2′-hydroxy-4′-n-hexyloxyphenyl)-6-(2′,4′-di(n-hexyloxy)phenyl)-1,3,5-triazine (Compound 27) of m.p. 85-87° C.

Workup

  1. customis held at 80° C
  2. temperatureAfter cooling
  3. filtrationAfter 24 hours at 25° C. the precipitate is filtered off
  4. washwashed with water (300 ml)
  5. customdried
  6. wash[2.5 kg of silica gel 60 (230-400 mesh), Ø=13 cm; h=60 cm; eluted with hexane/ethyl acetate (39:1)]
  7. customRemoval of the solvent from the main fraction

Sources & evidence

ORD record
ord-1ae4891838cb4533989563dd8ff99457
Source dataset
uspto-grants-2001_02
Patent number
US06184375B2

Reaction notes

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