Hydrochloric Acid → 1-(3-Bromo-4-hydroxyphenyl)propan-2-one

HRID 1375986Notes

Reaction equation

HRID 1375986 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[Na+].[Br:6][C:7]1[CH:8]=[C:9]([CH2:14]C(O)=O)[CH:10]=[CH:11][C:12]=1[OH:13].[OH-].[Na+].Cl>C(OC(=O)C)(=O)C>[Br:6][C:7]1[CH:8]=[C:9]([CH2:14][C:1]([CH3:2])=[O:4])[CH:10]=[CH:11][C:12]=1[OH:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 27696283-Bromo-4-hydroxyphenylacetic acid

Product 1

HCID 247210551-(3-Bromo-4-hydroxyphenyl)propan-2-oneYield 78.6%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Sodium acetate (50.5 g) was added to a solution of 3-bromo-4-hydroxyphenylacetic acid (28.5 g) in acetic anhydride (100 ml) and the mixture was refluxed with heating for 21 hours. After cooling to room temperature, 20% aqueous solution of sodium hydroxide was added to the reaction mixture to adjust to pH 11. The mixture was refluxed with heating for one hour. After cooling to room temperature, 10% aqueous solution of hydrochloric acid was added to the reaction mixture to adjust to pH 6. The mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous solution of sodium bicarbonate, and saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-n-hexane) to obtain 1-(3-bromo-4-hydroxyphenyl) acetone (22.2 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 21 hours
  3. temperatureThe mixture was refluxed
  4. temperaturewith heating for one hour
  5. temperatureAfter cooling to room temperature
  6. extractionThe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water, saturated aqueous solution of sodium bicarbonate, and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-6aef4f8b17ea4496af0760f8ad39c56c
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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