Reaktion #417961

Reaktionsgleichung

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

Psi

→

title compound

Ausbeute 70.0%

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

Ausbeute 70.0%

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationUpon completion the reaction was filtered over celite
2. 2
   workup.ADDITIONdiluted
3. 3
   SonstigeThe acetic acid was removed in vacuo
4. 4
   workup.ADDITIONThe resulting oil was diluted with ethyl acetate
5. 5
   Waschenwas washed three times with water
6. 6
   TrocknenThe organic layer was dried over sodium sulfate
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe crude compound was purified via flash chromatography with 100% ethyl acetate

Vorschrift

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.

Quelle