Sodium Hydroxide → 2-(4-(Ethanesulfonyl)phenyl)acetic acid

HRID 1777820Notes

Reaction equation

HRID 1777820 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])=[CH:8][CH:7]=1)C.[OH-].[Na+]>CCO.O>[CH2:15]([S:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:17])=[O:3])=[CH:7][CH:8]=1)(=[O:14])=[O:13])[CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58860788Ethyl 2-(4-(ethylsulfonyl)phenyl)acetate

Product 1

HCID 43298292-(4-(Ethanesulfonyl)phenyl)acetic acidYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl2-(4-(ethylsulfonyl)phenyl)acetate (10.0 g, 39 mmol) in EtOH (100 mL) was added a solution of NaOH (5.7 g, 142.5 mmol) in water (100 mL). The reaction mixture was stirred at rt for 16 h. EtOH was removed under reduced pressure. The aqueous layer was adjusted to pH=1 with 6 N aq. HCl and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine (2×100 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the desired product 2-(4-(ethylsulfonyl)phenyl)acetic acid (7.3 g, 82%) as a white solid. LC-MS tR=0.573 min in 5-95AB—1.5 min chromatography (Welch Xtimate C18, 2.1*30 mm, 3 um), MS (ESI) m/z 228.8 [M+H]+. 1H NMR (CDCl3 400 MHz): δ 7.88 (d, J=8.0 Hz, 2H), 7.50 (d, J=8.4 Hz, 2H), 3.77 (s, 2H), 3.12 (q, J=7.6 Hz, 2H), 1.28 (t, J=7.6 Hz, 3H).

Workup

  1. customEtOH was removed under reduced pressure
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic layers were washed with brine (2×100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-93075a13e74048ca957e75e66a1c0c61
Source dataset
uspto-grants-2016_02
Patent number
US09266886B2

Reaction notes

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