Acetic Acid → 6-(Benzenesulphonylmethyl)-3-ethyl-2-methoxy-benzoic acid

HRID 2177666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2177666
OO.[C:3]1([S:9][CH2:10][C:11]2[C:16]([C:17]([O:19]CC)=[O:18])=[C:15]([O:22][CH3:23])[C:14]([CH2:24][CH3:25])=[CH:13][CH:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-:26].[Li+].C(O)(=[O:30])C>O1CCOCC1.O>[C:3]1([S:9]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:22][CH3:23])[C:14]([CH2:24][CH3:25])=[CH:13][CH:12]=2)(=[O:30])=[O:26])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 67107436Ethyl 6-(phenylthiomethyl)-3-ethyl-2-methoxybenzoate2×

Produkt 1

HCID 529138626-(Benzenesulphonylmethyl)-3-ethyl-2-methoxy-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Hydrogen peroxide (30% aqueous solution, 0.117 ml) was added to a solution of ethyl 6-(phenylthiomethyl)-3-ethyl-2-methoxybenzoate (Intermediate 19, 0.057 g) in acetic acid (1.7 ml) and the resultant solution was stirred and heated at 60° C. for 2 hours. After cooling, the solution was evaporated to dryness to give the crude sulphone. The residue was dissolved in a mixture of dioxane (1 ml) and water (1 ml) and lithium hydroxide (0.072 g) was added. The mixture was stirred and heated in the microwave at 160° C. for 15 minutes. After cooling, the mixture was evaporated to dryness and the residue was acidified by addition of hydrochloric acid (1M) and then immediately purified by preparative HPLC (C18) eluting with a mixture of methanol and water containing 0.1% formic acid to give 6-(benzenesulphonylmethyl)-3-ethyl-2-methoxy-benzoic acid (0.022 g) as a white solid.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe solution was evaporated to dryness
  3. customto give the crude sulphone
  4. additionwas added
  5. temperatureheated in the microwave at 160° C. for 15 minutes
  6. temperatureAfter cooling
  7. customthe mixture was evaporated to dryness
  8. additionthe residue was acidified by addition of hydrochloric acid (1M)
  9. customimmediately purified by preparative HPLC (C18)
  10. washeluting with a mixture of methanol and water containing 0.1% formic acid

Quellen und Nachweise

ORD-Eintrag
ord-63061ef805dd4d969c641f917f417588
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067905B2

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