Lithium hydroxide, monohydrate → 3-Methoxy-5-methylsulfonylbenzoic acid

HRID 1373106Notes

Reaction equation

HRID 1373106 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:12]=1)[C:6]([O:8]C)=[O:7].O.[OH-].[Li+]>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:12]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21074200Methyl 3-methoxy-5-(methylsulfonyl)benzoate

Product 1

HCID 210741983-Methoxy-5-methylsulfonylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 3-methoxy-5-methylsulfonylbenzoate (D14) (2.94 g) was dissolved in dioxan (18 ml) and lithium hydroxide monohydrate (0.762 g) in water (18 ml) was added. The mixture was stirred at room temperature for 2 h and then sufficient Amberlyst-15 H+ resin was added to adjust the pH to ˜4. The resin was removed by filtration and washed well with dioxan and the combined filtrates were evaporated. The residue was triturated with ether to give D15 as a pale buff solid (2 crops, 2.29 g).

Workup

  1. additionsufficient Amberlyst-15 H+ resin was added
  2. customThe resin was removed by filtration
  3. washwashed well with dioxan
  4. customthe combined filtrates were evaporated
  5. customThe residue was triturated with ether
  6. customto give D15 as a pale buff solid (2 crops, 2.29 g)

Sources & evidence

ORD record
ord-b18111341b304f2986d01d0d1a4d4a4f
Source dataset
uspto-grants-2007_01
Patent number
US07160905B2

Reaction notes

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