反応 #313001

反応方程式

4-hydroxy-3-methylbenzaldehyde

hydroxyl ammonium chloride

→

title compound

収率 66.0%

4-Hydroxy-3-methylbenzonitrile

収率 66.0%

溶媒

diethyl ether

acetic acid

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度under reflux for 90 minutes
3. 3
   その他The cooled reaction mixture
4. 4
   洗浄washed with water (30 mL)
5. 5
   洗浄The combined organic solution was washed with brine
6. 6
   乾燥dried over magnesium sulfate
7. 7
   濃縮concentrated in vacuo
8. 8
   その他the residue was purified by column chromatography on silica gel
9. 9
   洗浄eluting with dichloromethane

実験手順

A mixture of 4-hydroxy-3-methylbenzaldehyde (530 mg, 3.91 mmol) and hydroxyl ammonium chloride (406 mg, 5.81 mmol) in acetic acid (5 mL) was heated under reflux for 90 minutes. The cooled reaction mixture was then diluted with diethyl ether (30 mL) and washed with water (30 mL). The combined organic solution was washed with brine, dried over magnesium sulfate, concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol, 100:0 to 97.5:2.5, to afford the title compound as a pale yellow oil in 66% yield, 345 mg.

出典