Hydrochloric Acid → 4-(Propane-2-sulfinyl)benzoic acid

HRID 1908130Notes

Reaction equation

HRID 1908130 reaction equation
[CH:1]([S:4]([C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][CH:7]=1)=[O:5])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CCO>[CH:1]([S:4]([C:6]1[CH:16]=[CH:15][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)=[O:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58550716HCID 58550716, compound

Product 1

HCID 535369704-(Propane-2-sulfinyl)benzoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl 4-isopropylsulfinylbenzoate (245 mg, 1.02 mmol) in EtOH (1 mL) at room temperature was added NaOH (300 μL of 5.0 M, 1.50 mmol) dropwise and the mixture stirred for 30 min. The pH of the mixture was adjusted to 2 with 1N HCl before it was evaporated to dryness. The solids were taken up in water, filtered, washed with water (2×), and desiccated to give 4-isopropylsulfinylbenzoic acid (80%) as a white solid. 1H NMR (400 MHz, DMSO) δ 13.30 (s, 1H), 8.11 (d, J=8.2 Hz, 2H), 7.73 (d, J=8.2 Hz, 2H), 3.07-2.97 (m, 1H), 1.22 (d, J=6.9 Hz, 3H), 0.90 (d, J=6.7 Hz, 3H).

Workup

  1. customwas evaporated to dryness
  2. filtrationfiltered
  3. washwashed with water (2×)

Sources & evidence

ORD record
ord-a9b5d421b16d4a1886fc2bcea8ab5b91
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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