Reaktion #1242514

Reaktionsgleichung

sodium hypochlorite

2-carbamoyl-benzyl alcohol

isopropyl acetate

→

desired product

Ausbeute 70.0%

2-oxo-dihydrobenzo[d][1,3]oxazine

Ausbeute 70.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled in a water bath
2. 2
   TemperaturVigorous agitation was maintained during the addition and for a further 2 hours
3. 3
   SonstigeThe two-phase reaction mixture
4. 4
   workup.DISSOLUTIONto dissolve all solids
5. 5
   SonstigeThe organic phase was separated
6. 6
   workup.DISTILLATIONthe medium distilled off
7. 7
   SonstigeThe formed solid was recrystallized from 3 volumes of toluene

Vorschrift

143 g (0.948 moles) of 2-carbamoyl-benzyl alcohol, 2.3 g (0.0226 moles) of sodium bromide, 6.7 g of Adogen 464 and 806 ml of isopropyl acetate were stirred together in a two liter flask and cooled in a water bath. 504 ml of a 14% w/v solution of sodium hypochlorite (1.0 mole) was added to the stirred mixture over 40 minutes and at 30° C. Vigorous agitation was maintained during the addition and for a further 2 hours. The two-phase reaction mixture was then warmed to 50° C. to dissolve all solids. The organic phase was separated and the medium distilled off. The formed solid was recrystallized from 3 volumes of toluene to form 99 g of the desired product as a pale brown solid; m.p. 112° C.; yield 70%.

Quelle