Reaktion #489322

Reaktionsgleichung

Triethylamine

3-methoxy-2-methylbenzoic acid

t-BuOH

dppa

→

target product

Ausbeute 103.0%

N-(tert-butyloxycarbonyl)-3-methoxy-2-methylaniline

Ausbeute 103.0%

Lösungsmittel

toluene

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA clear solution was obtained
2. 2
   workup.WAITat 100° C. for 1 h
3. 3
   Temperaturthe resulting mixture was refluxed for 7 h
4. 4
   TemperaturThe solution was cooled to room temperature
5. 5
   Waschenthen successively washed with water, 0.5 N HCl, 0.5 N NaOH and brine
6. 6
   Trocknendried (Na2SO4)
7. 7
   Sonstigeevaporated

Vorschrift

Triethylamine (42.4 mL, 302 mmol) was added to a suspension of 3-methoxy-2-methylbenzoic acid (45.6 g, 274 mmol) in dry toluene (800 mL). A clear solution was obtained. Then, dppa (65.4 mL, 302 mmol) in toluene (100 mL) was slowly added. After 1 h at room temperature, the reaction mixture was successively heated at 50° C. for 0.5 h, at 70° C. for 0.5 h then at 100° C. for 1 h. To this solution, t-BuOH (30.5 g, 411 mmol) in toluene (40 mL) was added at 100° C. and the resulting mixture was refluxed for 7 h. The solution was cooled to room temperature then successively washed with water, 0.5 N HCl, 0.5 N NaOH and brine, dried (Na2SO4), and evaporated to give 67 g of the target product: m/z=237 (M)+.

Quelle