Potassium Carbonate → HCID 69117522, compound

HRID 902346Notes

Reaction equation

HRID 902346 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8]C)[C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16].C(=O)([O-])[O-].[K+].[K+]>Br.O.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 68964104HCID 68964104, compound

Product 1

HCID 69117522HCID 69117522, compoundYield 77.3%

Reagents, catalysts & solvents 3

HCID 260Hydrogen BromideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Chloro-6-methoxy-2′-methylbiphenyl (15.0 g, 64.5 mmol) was heated in hydrogen bromide (33% in acetic acid, 60 mL) at 65° C. overnight. The resulting mixture was cooled to room temperature, poured in water and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue oil was further treated with potassium carbonate (10.5 g, 75.6 mmol) in methanol (100 mL) at room temperature for 2 h. The solvent was removed under reduced pressure. The residue was extracted with ethyl acetate and the organic layer was washed with water and saturated sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by ISCO using a solvent gradient of 10 to 40% ethyl acetate in hexanes produced 10.9 g (77%) of 6-chloro-2′-methyl-biphenyl-2-ol as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe solvent was removed under reduced pressure
  7. extractionThe residue was extracted with ethyl acetate
  8. washthe organic layer was washed with water and saturated sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customPurification by ISCO

Sources & evidence

ORD record
ord-99696d70173b4c4bba5f3e071e60a671
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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