Sodium Hydroxide → 3-(Methylthio)benzoic Acid

HRID 732021

Reaktionsgleichung

Reaktionsgleichung von HRID 732021
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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 2203293-(Methylthio)benzoic AcidAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1221c9dbbc8e4546a1539b6b538ac032
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585881B2

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