تفاعل #417961

معادلة التفاعل

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

Psi

→

title compound

المردود 70.0%

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

المردود 70.0%

المذيبات

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر