Sulfuric Acid → 2-Acetoxy-3-chloro-benzoic acid

HRID 2190906Notes

Reaction equation

HRID 2190906 reaction equation
[OH:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](OC(=O)C)(=[O:14])[CH3:13].OS(O)(=O)=O>>[C:12]([O:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:14])[CH3:13]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 745853-Chlorosalicylic acid

Product 1

HCID 181834362-Acetoxy-3-chloro-benzoic acidYield 94.6%

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-hydroxy-3-chloro-benzoic acid (5.0 g, 29.0 mmol) in acetic anhydride (9.0 mL, 95.6 mmol) was added conc. H2SO4 (0.44 mL) at rt. Resulting suspension was heated in a 100° C. oil bath for 40 min. After cooled to about 50° C., the reaction mixture was poured onto ice (100 g) with stirring. Liquid was decanted off and the gooey residue was dissolved in methylene chloride, washed with water and brine, and dried over MgSO4. It was then filtered, and concentrated to give the title compound (5.89 g). 1H NMR (200 MHz, CDCl3): δ (ppm)=7.99 (dd, J=7.8, 1.6 Hz, 1H), 7.66 (dd, J=7.8, 1.6 Hz, 1H), 7.28 (m, 1H), 2.39 (s, 3H).

Workup

  1. customResulting suspension
  2. temperatureAfter cooled to about 50° C.
  3. additionthe reaction mixture was poured onto ice (100 g)
  4. customLiquid was decanted off
  5. dissolutionthe gooey residue was dissolved in methylene chloride
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationIt was then filtered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-bbedcedd2850448cbea0c92fba9b1dde
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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