反応 #65902

反応方程式

methyl-t-butyl ether

sodium cyanide

sodium bisulfite

p-anisaldehyde

→

p-methoxybenzaldehyde cyanohydrin

溶媒

water

Water

反応条件

後処理

1. 1
   温度The slurry is cooled to 5° C.
2. 2
   workup.STIRRINGThe reaction is stirred for 2 hrs
3. 3
   温度at 5° C., then warmed to room temperature
4. 4
   その他The layers are separated after a brief stir
5. 5
   抽出the aqueous phase re-extracted with MTBE (100 ml)
6. 6
   乾燥The combined organic layers were dried (MgSO4)
7. 7
   濃縮concentrated to an oil, which
8. 8
   その他to afford product
9. 9
   その他The material can be recrystallized from toluene (3 ml per g substrate, heat to 35° C., cool to 5° C., 90% recovery)

実験手順

Water (720 ml), sodium bisulfite (81 g, 0.775 mol, 1.2 equiv) and p-anisaldehyde (88 g, 0.646 mol, 1.0 equiv) are combined, warmed to 40° C. and stirred for 3 hrs. The slurry is cooled to 5° C., and sodium cyanide (35 g, 0.711 mol, 1.1 equiv) in 140 ml water is added. The reaction is stirred for 2 hrs. at 5° C., then warmed to room temperature, and methyl-t-butyl ether (MTBE) (400 ml) added. The layers are separated after a brief stir, and the aqueous phase re-extracted with MTBE (100 ml). The combined organic layers were dried (MgSO4), and concentrated to an oil, which was seeded to afford product: 69.5 g, 65.9%. The material can be recrystallized from toluene (3 ml per g substrate, heat to 35° C., cool to 5° C., 90% recovery).

出典