Potassium Carbonate → HCID 117833308, compound

HRID 924536Notes

Reaction equation

HRID 924536 reaction equation
O[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[C:17](=[O:20])([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][Br:32]>CC(C)=O>[Br:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:15]=[CH:16][C:2]([O:20][CH2:17][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][Br:32])=[CH:3][CH:4]=2)=[O:7])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 691504,4'-DihydroxybenzophenoneHCID 783101,8-Dibromooctane

Product 1

HCID 117833308HCID 117833308, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 4,4′-dihydroxybenzophenone (1.0 g, 4.7 mmol) and potassium carbonate (1.3 g, 9.3 mmol) in acetone (50 mL) was added 1,8-dibromooctane (3.8 g, 14.0 mmol). The mixture was refluxed under stirring for 12 h. After filtration and solvent evaporation, the crude product was purified by a silica gel column using chloroform as eluent. 4,4′-bis(8-bromooctyloxy)benzophenone was obtained as white powder in 66% yield (3.10 g). Rf=0.5 (chloroform). NMR (400 MHz, CDCl3), δ (ppm): 7.78 (d, 4H), 6.94 (d, 4H), 4.05 (t, 4H), 3.42 (t, 4H), 1.89□1.80 (m, 8H), 1.48-1.39 (m, 16H). 13C NMR (100 MHz, CDCl3), δ (ppm): 193.9, 161.8, 131.6, 129.9, 113.3, 67.5, 33.3, 32.1, 28.5, 28.4, 28.0, 27.4, 25.3.

Workup

  1. temperatureThe mixture was refluxed
  2. filtrationAfter filtration and solvent evaporation
  3. customthe crude product was purified by a silica gel column

Sources & evidence

ORD record
ord-a618d0353b834676abab0e8285fc11a7
Source dataset
uspto-grants-2016_03
Patent number
US09279806B2

Reaction notes

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