Sodium Hydroxide → 3-(Methylthio)benzoic Acid

HRID 273109Notes

Reaction equation

HRID 273109 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][CH3:11])[CH:5]=1.[OH-].[Na+]>CO.C1COCC1>[CH3:11][S:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:12])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 6432769Methyl 3-(methylthio)benzoate

Product 1

HCID 2203293-(Methylthio)benzoic AcidYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Methylsulfanyl-benzoic acid methyl ester (684 mg, 3.8 mmol) and 1N NaOH (5.6 mL, 5.6 mmol) in methanol (8 mL) and THF (8 mL) were heated at 70° C. for 1 hour. The reaction mixture was concentrated and then the residue was diluted with water. After acidification with 1N HCl to pH˜2, the aqueous layer was extracted with ethyl acetate and then washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 3-methylsulfanyl-benzoic acid (616 mg, 97%, white solid). 1H NMR (DMSO), δ (ppm): 13.1 (bs, 1H), 7.76 (s, 1H), 7.70 (d, 1H), 7.51 (d, 1H), 7.44 (t, 1H), 2.52 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with water
  3. extractionAfter acidification with 1N HCl to pH˜2, the aqueous layer was extracted with ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fa95748298f343c7905764149a015e9c
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Reaction notes

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