反応 #417961

反応方程式

N-(3-Hydroxy-4-(1-hydroxybutyl)phenyl)acetamide

Psi

→

title compound

収率 70.0%

N-(4-butyl-3-hydroxyphenyl)acetamide

収率 70.0%

溶媒

反応条件

後処理

1. 1
   ろ過Upon completion the reaction was filtered over celite
2. 2
   workup.ADDITIONdiluted
3. 3
   その他The acetic acid was removed in vacuo
4. 4
   workup.ADDITIONThe resulting oil was diluted with ethyl acetate
5. 5
   洗浄was washed three times with water
6. 6
   乾燥The organic layer was dried over sodium sulfate
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The crude compound was purified via flash chromatography with 100% ethyl acetate

実験手順

N-(3-Hydroxy-4-(1-hydroxybutyl)phenyl)acetamide (184 g) was reduced in 20 g batches by dissolving it in de-oxygenated acetic acid (210 mL) in the presence of 10% Pd/C (7 g) at 60 Psi in a Parr hydrogenator for eleven hrs. Upon completion the reaction was filtered over celite and diluted. The acetic acid was removed in vacuo. The resulting oil was diluted with ethyl acetate and was washed three times with water and once with brine. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude compound was purified via flash chromatography with 100% ethyl acetate to obtain the title compound in 70% yield (120 g) as a waxy tan solid.

出典