Sodium Hydroxide → 3-[(Methylsulfonyl)oxy]benzoic acid

HRID 502405Notes

Reaction equation

HRID 502405 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH:5]=1.[OH-].[Na+]>C1COCC1.C(O)C>[CH3:14][S:11]([O:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:15])=[O:2])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 104438313-methanesulfonyloxy-benzoic acid methyl ester

Product 1

HCID 184757433-[(Methylsulfonyl)oxy]benzoic acidYield 97.7%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The above prepared 3-methanesulfonyloxy-benzoic acid methyl ester (3.81 g, 16 mmol) was dissolved in 100 ml of THF/ethanol=1/1 and treated with 50 ml of aq. NaOH (1M, 3 eq.). The mixture was stirred for 2 h at ambient temperature and was then poured onto crashed ice/AcOEt/HCl dil.; the organic layer was washed with water, dried over sodium sulfate, and evaporated to dryness to leave 3.38 g of the title compound as white solid.

Workup

  1. additionwas then poured
  2. washthe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-daf0b81ed6df40e2a16298a968516ba7
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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