Sulfuric Acid → 3-Acetoxybenzoic acid

HRID 1003356Notes

Reaction equation

HRID 1003356 reaction equation
S(=O)(=O)(O)O.[OH:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11].[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[C:16]([O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])(=[O:18])[CH3:17]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 74203-Hydroxybenzoic AcidHCID 7918Acetic Anhydride

Product 1

HCID 2386693-Acetoxybenzoic acid

Conditions

Temperature
60 °C

Procedure

Concentrated sulfuric acid (0.2 ml) was added to a solution of 10.07 g (72.9 mol) of 3-hydroxybenzoic acid in 10 ml of acetic anhydride. The resulting mixture was stirred at 60° C. for 1 hour and was then allowed to stand overnight at room temperature. The resulting precipitate was collected by filtration, washed with benzene, and then dried in air. The precipitate was recrystallized from acetone-hexane, whereby 8.92 g of 3-acetoxybenzoic acid were obtained as colorless prisms (yield: 67.9%, melting point: 149-151° C.). A mixture of 8.92 g (49.5 mmol) of 3-acetoxybenzoic acid and 26.33 g (198 mmol) of aluminum chloride was then heated at 160° C. for 3 hours. Subsequent to the addition of ice and 1N hydrochloric acid, the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and was then dried over MgSO4. The solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol, whereby 1.61 g of the title compound were obtained as pale yellow powder (yield: 18%).

Workup

  1. waitto stand overnight at room temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with benzene
  4. customdried in air
  5. customThe precipitate was recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-4be2263b36b443e391b5533f38af85ae
Source dataset
uspto-grants-2000_04
Patent number
US06046212

Reaction notes

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