Sodium Bicarbonate → HCID 12179907, compound

HRID 1691784Notes

Reaction equation

HRID 1691784 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=[O:13].[C:15](=O)(O)[O-].[Na+]>CO.OS(O)(=O)=O>[CH3:15][O:13][C:12](=[O:14])[CH2:11][C:3]1[CH:4]=[C:5]([OH:10])[C:6]([O:8][CH3:9])=[CH:7][C:2]=1[Br:1]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 13657735HCID 13657735, compound

Product 1

HCID 12179907HCID 12179907, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

(2-Bromo-5-hydroxy-4-methoxy-phenyl)-acetic acid (11 g) was dissolved in 150 ml methanol and 0.8 ml conc. H2SO4. The solution was stirred at room temperature for 18 hours. Saturated aqueous sodium bicarbonate solution was added until the mixture was basic and the mixture was concentrated under reduced pressure. The residue was partitioned between bicarbonate solution and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was taken up in ethyl acetate and crystallized by the addition of hexanes. Filtration gave 8.8 g (2-bromo-5-hydroxy-4-methoxy-phenyl)-acetic acid methyl ester.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between bicarbonate solution and ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customcrystallized by the addition of hexanes
  7. filtrationFiltration

Sources & evidence

ORD record
ord-b1e2a6c9fa784f3e996240f64a434a2f
Source dataset
uspto-grants-2012_04
Patent number
US08153808B2

Reaction notes

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