Reaktion #410573

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