Hydrogen Peroxide → HCID 68601368, compound

HRID 1951982Notes

Reaction equation

HRID 1951982 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][C:4]=1[CH:16]=[CH2:17].C12BC(CCC1)CCC2.[OH:27]O.[OH-].[Na+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][C:4]=1[CH2:16][CH2:17][OH:27]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 68601375HCID 68601375, compound

Product 1

HCID 68601368HCID 68601368, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3.9 g (16.4 mmol) of 2-methoxy-4-(2-methoxy-ethoxymethoxy)-1-vinyl-benzene diluted in 30 ml of tetrahydrofuran is added dropwise to a solution at room temperature of 4 g (16.4 mmol) of the dimer of 9-borabicyclo[3.3.1]nonane diluted in 10 ml of tetrahydrofuran. After stirring at room temperature for 20 hours, the above reaction mixture is cooled to 0° C. and 10 ml of water is added dropwise. The reaction mixture is stirred at room temperature for 1 hour and then cooled again to 0° C. and 10 ml of hydrogen peroxide is added. After stirring for 2 hours at room temperature, the reaction mixture is treated by adding 3 ml of an aqueous solution of sodium hydroxide of concentration 3M and stirred for 30 minutes. The reaction mixture is extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated. The raw product is purified by silica column chromatography, eluted with a heptane/ethyl acetate mixture 60/40 to give 3.3 g (78%) of 2-[2-methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-ethanol in the form of a light yellow oil.

Workup

  1. temperaturethe above reaction mixture is cooled to 0° C.
  2. stirringThe reaction mixture is stirred at room temperature for 1 hour
  3. temperaturecooled again to 0° C.
  4. stirringAfter stirring for 2 hours at room temperature
  5. additionthe reaction mixture is treated
  6. stirringstirred for 30 minutes
  7. extractionThe reaction mixture is extracted with ethyl acetate
  8. washwashed with saturated sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customThe raw product is purified by silica column chromatography
  13. washeluted with a heptane/ethyl acetate mixture 60/40

Sources & evidence

ORD record
ord-d63a2d0005f44fdebb16f160b500fd9a
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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