Potassium Iodide → 2,2',2''-((Ethane-1,1,1-triyltris(benzene-4,1-diyl))tris(oxy))tris(ethan-1-ol)

HRID 1506744Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH3:9])=[CH:4][CH:3]=1.[I-].[K+].C1(=O)[O:30][CH2:29][CH2:28]O1>CN(C=O)C>[OH:1][CH2:2][CH2:3][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:28][CH2:29][OH:30])=[CH:12][CH:11]=2)([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:12][CH2:13][OH:16])=[CH:21][CH:22]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 145 °C

Procedure

A 500 ml round bottom flask is equipped with a mechanical stirrer, thermometer and condenser. Add 50 grams 1,1,1-tris(4-hydroxyphenyl) ethane, 100 grams DMF, 0.5 g. potassium iodide and 47.4 grams of ethylene carbonate. Heat to 145° C. and hold for 6 hours. Add 200 g. ethyl acetate and wash the organic portion four times with 150 g. saturated brine. Strip the solvent from the mix on a rotary evaporator. The yield of tan solid is 78 grams. Recrystallize this crude product by dissolving in 300 g. boiling ethyl acetate and allowing to cool slowly. Collect 70.3 grams of a tan solid; the mp=78-81° C.

Workup

customA 500 ml round bottom flask is equipped with a mechanical stirrer
additionAdd 200 g
washethyl acetate and wash the organic portion four times with 150 g
additionStrip the solvent from the mix on a rotary evaporator
customRecrystallize this crude product
dissolutionby dissolving in 300 g
temperatureto cool slowly
customCollect 70.3 grams of a tan solid

Sources & evidence

ORD record: ord-9b7aa50b6e3b4a59abd3d054d3b86878
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221743B2

Reaction notes

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