Sulfuric Acid → 5-Bromo-2-acetylsalicylic acid

HRID 1003350Notes

Reaction equation

HRID 1003350 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:15]=[C:11]([C:12]([OH:14])=[O:13])[C:10]([OH:16])=[CH:9][CH:8]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>O>[C:17]([O:16][C:10]1[CH:9]=[CH:8][C:7]([Br:6])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 69725-Bromosalicylic acidHCID 7918Acetic Anhydride

Product 1

HCID 739225-Bromo-2-acetylsalicylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated sulfuric acid (0.5 ml) was added under stirring to a mixture of 100 g (0.46 mol) of 5-bromosalicylic acid and 105 ml of acetic anhydride. Several minutes later, 1,000 ml of water were added, and the resulting precipitate was collected by filtration and then washed with water. A white matter, which had been collected by filtration, was dissolved in 1,000 ml of ethyl acetate. The resulting solution was washed with a saturated aqueous solution of sodium chloride (2×300 ml) and was then dried over Na2SO4. The solvent was distilled off under reduced pressure, whereby 105 g of 2-acetyloxy-5-bromobenzoic acid were obtained as white crystals (yield: 88%).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water
  3. filtrationA white matter, which had been collected by filtration
  4. dissolutionwas dissolved in 1,000 ml of ethyl acetate
  5. washThe resulting solution was washed with a saturated aqueous solution of sodium chloride (2×300 ml)
  6. dry with materialwas then dried over Na2SO4
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ec9b886a52094e5599e85540946b5eb9
Source dataset
uspto-grants-2000_04
Patent number
US06046212

Reaction notes

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