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

HRID 2204213Notes

Reaction equation

HRID 2204213 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 dessicated 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-64e366e032d841bc8ca3fdd0044803b2
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

Loading…