S-Methyl methanethiosulfonate → 4-((Methyldisulfanyl)methyl)benzoic acid

HRID 1529512

Reaktionsgleichung

Reaktionsgleichung von HRID 1529512
[SH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[CH3:12][S:13]S(C)(=O)=O>O.C(O)C>[CH3:12][S:13][S:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1

Komponenten

5

Edukt 2

HCID 18064S-Methyl methanethiosulfonateHCID 5850394-(Mercaptomethyl)benzoic acid

Produkt 1

HCID 591569114-((Methyldisulfanyl)methyl)benzoic acidAusbeute 75,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

4-(mercaptomethyl)benzoic acid (36, 500 mg, 2.97 mmol) was dissolved in water (10 mL) and cooled in an ice bath. The cooled solution stirred as methyl methanethiolsulfonate (413 mg, 3.27 mmol) dissolved in ethanol (5.00 mL) was added. Following addition, the cooling bath was removed and the reaction was stirred overnight at room temperature. After proceeding overnight, the reaction was diluted with saturated sodium chloride and extracted with ether. The combined extracts were washed with sodium chloride, dried over anhydrous sodium sulfate and concentrated in vacuo. The product was isolated using silica flash chromatography eluting with a gradient of 40-60% ethyl acetate in hexanes containing 1% acetic acid over 20 min. to give 482 mg of the desired product, 4-((methyldisulfanyl)methyl)benzoic acid (37b), in 73.5% yield. 1H NMR (CDCl3) δ 2.121 (3H, s), 3.938 (2H, s), 7.457 (2H, d, J=8.4 Hz), 8.068 (2H, d, J=8 Hz).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. additionwas added
  3. additionaddition
  4. customthe cooling bath was removed
  5. waitAfter proceeding overnight
  6. additionthe reaction was diluted with saturated sodium chloride
  7. extractionextracted with ether
  8. washThe combined extracts were washed with sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe product was isolated
  12. washeluting with a gradient of 40-60% ethyl acetate in hexanes containing 1% acetic acid over 20 min.

Quellen und Nachweise

ORD-Eintrag
ord-f4e2517cde9c43b0b2cfba5a582449ec
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090629B2

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