Methanol → Methyl 4-sulfanylbenzoate

HRID 265436

Reaktionsgleichung

Reaktionsgleichung von HRID 265436
[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:16]O>>[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 957384-Mercaptobenzoic acid

Produkt 1

HCID 237573Methyl 4-sulfanylbenzoate

Versuchsvorschrift

To a solution of 4-mercaptobenzoic acid (Apin, 1.72 g, 11.17 mmol) in anhydrous methyl alcohol (20.0 mL) was added concentrated sulfuric acid (0.43 mL). The reaction mixture is then warmed to reflux for 16 h, concentrated in vacuo, diluted with ethyl acetate (100 mL) and washed with saturated sodium bicarbonate (2×100 mL). The organic phase is then separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 712 mg (Y: 38%) of the title product; 1H-NMR (CDCl3): δ 7.89 (d, J=8.7 Hz, 2H), 7.29 (d, J=8.7 Hz, 2H), 3.90 (s, 3H), 3.60 (s, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture is then warmed
  2. temperatureto reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. additiondiluted with ethyl acetate (100 mL)
  5. washwashed with saturated sodium bicarbonate (2×100 mL)
  6. customThe organic phase is then separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e50a276094814008b88cda2fade347e6
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648385

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