反応 #1595970

反応方程式

NH4OH

sulfuric acid

4-(4-aminophenyl)butyric acid

methanol

→

title compound

収率 96.0%

methyl 4-(4-aminophenyl)butanoate

収率 96.0%

溶媒

dichloromethane

THF

water

反応条件

後処理

1. 1
   温度to reflux for 1.5 h
2. 2
   workup.DISTILLATIONAfter this time, methanol (˜25 mL) was distilled off
3. 3
   workup.ADDITIONmethyl tert-butyl ether was added
4. 4
   温度to slowly cool to room temperature
5. 5
   workup.ADDITIONdiluted with hexanes (50 mL)
6. 6
   その他to afford a white solid
7. 7
   その他the layers separated
8. 8
   洗浄The organic layer was washed with saturated sodium chloride (5 mL)
9. 9
   乾燥dried over sodium sulfate
10. 10
    ろ過filtered
11. 11
    濃縮concentrated under reduced pressure

実験手順

A 250-mL round bottom flask was charged with 4-(4-aminophenyl)butyric acid (2.00 g, 11.2 mmol) in methanol (50 mL) and treated with conc. sulfuric acid (1 mL). The resultant mixture was heated to reflux for 1.5 h. After this time, methanol (˜25 mL) was distilled off. The reaction was cooled to 60° C. and methyl tert-butyl ether was added. The mixture was allowed to slowly cool to room temperature, then diluted with hexanes (50 mL) to afford a white solid. The solid was dissolved in THF (6 mL)/water (4 mL) and treated with conc. NH4OH (6 mL). The mixture was diluted with dichloromethane (50 mL) and the layers separated. The organic layer was washed with saturated sodium chloride (5 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound (2.07 g, 96%) as a brown solid. MW=193.24. 1H NMR (DMSO-d6, 500 MHz) δ 6.83-6.79 (m, 2H), 6.50-6.46 (m, 2H), 4.81 (s, 2H), 3.57 (s, 3H), 2.39 (t, J=7.5 Hz, 2H), 2.25 (t, J=7.5 Hz, 2H), 1.73 (quin, J=7.5 Hz, 2H).

出典