1-Bromooctadecane → 2,3,4-Trioctadecanoxybenzophenone

HRID 573965Notes

Reaction equation

HRID 573965 reaction equation
[OH:1][C:2]1[C:15]([OH:16])=[C:14](O)[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[C:37](=[O:40])([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:19]([O:1][C:2]1[C:15]([O:16][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19])=[C:14]([O:40][CH2:37][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 70837Alizarin Yellow A

Product 1

HCID 595103512,3,4-TrioctadecanoxybenzophenoneYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Under an argon atmosphere, 2,3,4-trihydroxybenzophenone (1.61 g, 7.00 mmol), 1-bromooctadecane (7.32 g, 22.0 mmol) and potassium carbonate (4.35 g, 31.5 mmol) were added to dehydrating N,N-dimethylformamide (30 mL), and the mixture was stirred at 80° C. overnight. After completion of the reaction, purified water (200 mL) was added to the reaction mixture, the mixture was stirred for 1 hr, and the precipitated solid was collected by filtration. The obtained solid was slurry-washed in methanol and, after filtration, dried under reduced pressure to give the title compound (6.31 g, 91.1%) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. custompurified water (200 mL)
  3. additionwas added to the reaction mixture
  4. stirringthe mixture was stirred for 1 hr
  5. filtrationthe precipitated solid was collected by filtration
  6. washThe obtained solid was slurry-washed in methanol
  7. filtrationafter filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-9c3ace18d0934304bb2c6f9ad57f2525
Source dataset
uspto-grants-2015_05
Patent number
US09029528B2

Reaction notes

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