3-Acetyl-5-bromo-2-hydroxybenzoic acid → 3-acetyl-2-hydroxybenzoic acid

HRID 876535Notes

Reaction equation

HRID 876535 reaction equation
[C:1]([C:4]1[C:5]([OH:14])=[C:6]([CH:10]=[C:11](Br)[CH:12]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]>C(O)C.[Pd]>[C:1]([C:4]1[C:5]([OH:14])=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 110106863-Acetyl-5-bromo-2-hydroxybenzoic acid

Product 1

HCID 108992643-acetyl-2-hydroxybenzoic acidYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-acetyl-5-bromo-2-hydroxybenzoic acid 31 (50 g, 0.19 mol) was dissolved in 250 mL ethanol. After addition of 5.0 g 10% Pd/C the reaction mixture was hydrogenated under 15 atm H2-pressure at room temperature for 6 h. The catalyst was filtered and the solvent was evaporated. The residue was poured into H2O and extracted with CH2Cl2. The combined organic phase was dried and the solvent was removed to give 32 (28 g, 85% yield)

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was evaporated
  3. additionThe residue was poured into H2O
  4. extractionextracted with CH2Cl2
  5. customThe combined organic phase was dried
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-43d3767f31fd48d9ab13f969cd83fe22
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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