Potassium Hydroxide → 5-Mesyl-o-anisic acid

HRID 2230600Notes

Reaction equation

HRID 2230600 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[K+]>>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 6454622Methyl 5-mesyl-o-anisate

Product 1

HCID 1708405-Mesyl-o-anisic acid

Procedure

Combine methyl 2-methoxy-5-methylsulfonylbenzoate (2.24 g, 9.2 mmol) and a 1 M aqueous potassium hydroxide solution (10 mL, 10 mmol). Heat to reflux. After 2 hours, filter while still hot, cool in an ice bath, and acidify by dropwise addition of a 1 M aqueous hydrochloric acid solution (11 mL) to give a solid. Collect the solid by filtration, rinse with water, and dry to give the title compound: mp; 189-191° C. Elemental Analysis Calculated for C9H10SO5: C, 46.95; H, 4.38. Found: C, 46.76; H, 4.40.

Workup

  1. temperatureHeat to reflux
  2. filtrationfilter while still hot,
  3. temperaturecool in an ice bath
  4. additionacidify by dropwise addition of a 1 M aqueous hydrochloric acid solution (11 mL)
  5. customto give a solid
  6. customCollect the solid
  7. filtrationby filtration
  8. washrinse with water
  9. customdry

Sources & evidence

ORD record
ord-dbd16ca92f114a18b36b74248165fc16
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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