Lithium hydroxide, monohydrate → 2-tert-Butoxy-5-methanesulfonyl-benzoic acid

HRID 1352253Notes

Reaction equation

HRID 1352253 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].O.[OH-].[Li+]>C1COCC1.O>[C:15]([O:14][C:5]1[CH:6]=[CH:7][C:8]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:9][C:4]=1[C:3]([OH:19])=[O:2])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 586778292-tert-Butoxy-5-methanesulfonyl-benzoic acid methyl ester

Product 1

HCID 211002592-tert-Butoxy-5-methanesulfonyl-benzoic acidYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 5.52 mmol 2-tert-butoxy-5-methanesulfonyl-benzoic acid methyl ester in 25 ml THF was added a solution of 8.34 mmol lithium hydroxide monohydrate in 25 ml water and the reaction mixture was stirred at room temperature for 4 hours. After such time the THF was removed in vacuo and to the remaining aqueous solution was added 8 ml of 1 N aq HCl leading to precipitation of the compound. The precipitate was filtered off and washed several times with water to yield the title compound (67%) as a white solid. MS (m/e): 289.9 (M+NH4+).

Workup

  1. customAfter such time the THF was removed in vacuo and to the remaining aqueous solution
  2. additionwas added 8 ml of 1 N aq HCl leading
  3. customto precipitation of the compound
  4. filtrationThe precipitate was filtered off
  5. washwashed several times with water

Sources & evidence

ORD record
ord-8d1255cd682f413e8e289b76d5628935
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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