Reaktion #724307

Reaktionsgleichung

methyl 2-methoxy-5-aminobenzoate

hydrochloric acid

sodium nitrite

sodium sulfide

sodium hydroxide

dimethylsulfate

hydrochloric acid

ethyl xanthic acid

sodium

sodium carbonate

→

methyl 2-methoxy-5-methylthiobenzoate

Lösungsmittel

ethyl acetate hexane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcool in an ice bath
2. 2
   workup.WAITAfter 2 hours
3. 3
   Sonstigeevaporate in vacuo
4. 4
   workup.WAITAfter 4 hours
5. 5
   Temperaturheat to reflux
6. 6
   workup.WAITAfter 24 hours
7. 7
   Extraktionextract with ethyl acetate
8. 8
   SonstigeSeparate the organic layer
9. 9
   Extraktionextract with brine
10. 10
    Trocknendry over Na2SO4
11. 11
    Filtrationfilter
12. 12
    Sonstigeevaporate in vacuo
13. 13
    Sonstigeto give a residue

Vorschrift

Alternately, combine methyl 2-methoxy-5-aminobenzoate (1.0 g, 5.6 mmol) and 12 M aqueous hydrochloric acid solution (1.2 g and cool in an ice bath. Add a solution of sodium nitrite (0.37-g, 5.3 mmol) in water (3 mL). After 1.5 hours, add ethyl xanthic acid, sodium salt (0.76 g, 6.3 mmol) and sodium carbonate (0.67 g, 6.3 mmol). After 2 hours, evaporate in vacuo and add sodium sulfide (0.69 g, 2.7 mmol) and a 1 M aqueous sodium hydroxide solution (10 mL). After 4 hours, add dimethylsulfate and heat to reflux. After 24 hours, cool to ambient temperature, acidify with 12 M hydrochloric acid solution and extract with ethyl acetate. Separate the organic layer, 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/hexane 2/1 to give methyl 2-methoxy-5-methylthiobenzoate. Elemental Analysis calculated for C9H12O3S: C, 54.53; H, 5.08. Found: C, 54.64; H, 4.95.

Quelle