Hydrochloric Acid → Methyl 2-methoxy-5-methylsulfinylbenzoate

HRID 323392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 323392
[CH3:1][O:2][C:3]1C=[CH:11][C:10](C)=[CH:9][C:4]=1C(OC)=S.[Br-].[Br-].[Br-].[C:17]1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[S:47](=[O:50])(O)[O-].[Na+].Cl.[C:53]([O:56][CH2:57]C)(=[O:55])[CH3:54]>O.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:9][C:10]([S:47]([CH3:17])=[O:50])=[CH:11][C:54]=1[C:53]([O:56][CH3:57])=[O:55]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 23665763Sodium BisulfiteHCID 53727199Methyl 2-methoxy-5-methylthiobenzoate

Produkt 1

HCID 18464431Methyl 2-methoxy-5-methylsulfinylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel3×HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Combine methyl 2-methoxy-5-methylthiobenzoate (3.0 g, 14.1 mmol), pyridine (10 mL) and water (10 mL). Cool in an ice bath. Add portionwise phenyltrimethylammonium tribromide (5.84 g, 15.5 mmol). After 30 minutes, warm to ambient temperature. After 3 hour, add a solution of sodium bisulfite (1.6 g) in water (4 mL). After 10 minutes, add a 12 M aqueous hydrochloric acid solution (11 mL) and water. Extract the reaction mixture four times with dichloromethane. Combine the organic layers, extract with brine, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give methyl 2-methoxy-5-methylsulfinylbenzoate: mp; 64-66° C. Elemental Analysis calculated for C9H12O4S: C, 52.62; H, 5.30. Found: C, 52.51; H, 5.37.

Aufarbeitung

  1. temperatureCool in an ice bath
  2. waitAfter 3 hour
  3. waitAfter 10 minutes
  4. extractionExtract the reaction mixture four times with dichloromethane
  5. extractionextract with brine
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. customevaporate in vacuo
  9. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-94b1198f11fe470e95e154c23c4c7cdf
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211199B1

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