Reaktion #2317780

Reaktionsgleichung

methyl 2-methoxy-5-methylthiobenzoate

sodium bisulfite

hydrochloric acid

phenyltrimethylammonium tribromide

ethyl acetate

→

methyl 2-methoxy-5-methylsulfinylbenzoate

Lösungsmittel

water

water

water

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturCool in an ice bath
2. 2
   workup.WAITAfter 3 hour
3. 3
   workup.WAITAfter 10 minutes
4. 4
   ExtraktionExtract the reaction mixture four times with dichloromethane
5. 5
   Extraktionextract with brine
6. 6
   Trocknendry over Na2SO4
7. 7
   Filtrationfilter
8. 8
   Sonstigeevaporate in vacuo
9. 9
   Sonstigeto give a residue

Vorschrift

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.

Quelle