Potassium Hydroxide → 5-Mesyl-o-anisic acid

HRID 323395Notes

Reaction equation

HRID 323395 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.

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-51e6a8f6e2ec4f5b836d67b9f2ad5d02
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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