Réaction #417961

Équation de réaction

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

Psi

→

title compound

Rendement 70.0%

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

Rendement 70.0%

Solvants

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source