Hydroquinone → HCID 24744926, compound

HRID 533892Notes

Reaction equation

HRID 533892 reaction equation
[C:1]1([OH:8])[CH:6]=[CH:5][C:4]([OH:7])=[CH:3][CH:2]=1.CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24]>CC(=O)OCC.O>[CH3:24][CH:23]([CH3:25])[CH2:22][CH2:21][O:7][C:4]1[CH:5]=[CH:6][C:1]([OH:8])=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 6228DimethylformamideHCID 78911-Bromo-3-methylbutaneHCID 10796Cesium carbonate

Product 1

HCID 24744926HCID 24744926, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of benzene-1,4-diol (20.0 g), DMF (100 mL), cesium carbonate (59.2 g) and 1-bromo-3-methyl-butane (13.7 g) was heated to 60° C. for 12 hours. After the mixture reached room temperature, it was distributed between water and EA. The organic phase was washed twice (water), dried (Na2SO4) and concentrated. The residue was purified by chromatography (SiO2; EA/heptane 1:2) to provide the subtitle compound.

Workup

  1. customreached room temperature
  2. washThe organic phase was washed twice (water)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (SiO2; EA/heptane 1:2)

Sources & evidence

ORD record
ord-3f8efbc07f614765ada3dcc8102b5ca1
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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