Hydrochloric Acid → 2-Hydroxy-4-((1-(methylsulfonyl)piperidin-4-yl)oxy)benzoic acid

HRID 454487Notes

Reaction equation

HRID 454487 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:13]=[C:12]([O:14][CH:15]2[CH2:20][CH2:19][N:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:17][CH2:16]2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7].O.Cl>O1CCOCC1.CO.C(OCC)(=O)C>[OH:3][C:4]1[CH:13]=[C:12]([O:14][CH:15]2[CH2:16][CH2:17][N:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:19][CH2:20]2)[CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 66990733Methyl 2-hydroxy-4-((1-(methylsulfonyl)piperidin-4-yl)oxy)benzoate

Product 1

HCID 669904182-Hydroxy-4-((1-(methylsulfonyl)piperidin-4-yl)oxy)benzoic acidYield 99%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A 2 mol/L aqueous solution of sodium hydroxide (0.87 mL) was added to a solution mixture of the obtained methyl 2-hydroxy-4-((1-(methylsulfonyl)piperidin-4-yl)oxy)benzoate (0.19 g) in dioxane (0.95 mL) and methanol (0.95 mL), followed by stirring at room temperature for 3 hours. A 2 mol/L aqueous solution of sodium hydroxide (0.58 mL) was added to the reaction mixture, followed by heating to reflux for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then water was added thereto. After adjusting the pH to 3 with 6 mol/L hydrochloric acid, ethyl acetate was added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 0.18 g of 2-hydroxy-4-((1-(methylsulfonyl)piperidin-4-yl)oxy)benzoic acid as a white solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 1 hour and 30 minutes
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additionwas added
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f5189a7db90f4112864898cab7bcf776
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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