1-Bromo-2-methylpropane → 1,2-Bis(4-isobutoxyphenyl)ethane-1,2-dione

HRID 530418

Reaction equation

HRID 530418 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[C:9]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH:27]([CH3:29])[CH3:28]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:26]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:18])[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:4][CH:5]([CH3:8])[CH3:6])=[CH:13][CH:12]=2)=[O:10])=[CH:6][CH:7]=1)[CH:27]([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 4582044,4'-Dihydroxybenzil

Product 1

HCID 1176004381,2-Bis(4-isobutoxyphenyl)ethane-1,2-dioneYield 212.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

1,2-Bis(4-hydroxyphenyl)ethane-1,2-dione (0.77 g, 3.18 mmol) was dissolved in 20 mL of DMF. Potassium carbonate (1.3 g, 9.4 mmol), tetrabutylammonium bromide (0.5 g, 1.55 mmol) and 1-bromo-2-methylpropane (0.86 mL, 7.91 mmol) were added, then the reaction was stirred at 130° C. overnight. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried over sodium sulfate. Concentration under vacuum gave the title compound as oil (1.2 g, quantitative).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-db3d9c4942684569a92fbb51e49d6c6c
Source dataset
uspto-grants-2016_05
Patent number
US09353089B2

Linked notes

Loading…