Hydrogen Peroxide → HCID 90460212, compound

HRID 588816Notes

Reaction equation

HRID 588816 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH:10]=[CH2:11])=[CH:4][C:3]=1[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[Cl:19].[OH-:20].[Na+].OO>C1COCC1.O>[Cl:19][C:13]1[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=1[C:3]1[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH3:9])=[C:5]([CH2:10][CH2:11][OH:20])[CH:4]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 117607167HCID 117607167, compound

Product 1

HCID 90460212HCID 90460212, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2,2′,5′-trichloro-4-methoxy-5-vinyl-1,1′-biphenyl (310 mg, 1 mmol) in THF (15 mL) under nitrogen at room temperature, BH3 (2 mL, 1N) was added. After stirring for 8 h, a mixture of NaOH (160 mg, 4 mmol) in water (3 mL) and H2O2 (30% in H2O, 0.3 g, 4 mmol) was added and the resulting mixture was stirred for 6 h. The reaction was quenched with NaHCO3 aqueous solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=4:1) to afford the desired product (180 mg, 54% yield) as a colorless oil.

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred for 6 h
  3. customThe reaction was quenched with NaHCO3 aqueous solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-dfefcdeeaa5d42bba9d4bf7da0ab2c29
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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