Réaction #46726

Équation de réaction

sesamol

DMF

sodium hydride

1-bromooctane

→

white solid

4-Octyloxy-benzo[1,3]dioxole

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   workup.ADDITIONpoured onto H2O
3. 3
   Extractionextracted with diethylether (2×)
4. 4
   SéchageThe combined organic fractions were dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated in vacuo

Mode opératoire

A solution of sesamol (6.9 g; 50 mmol) in DMF (100 mL) under N2 was cooled to 0° C. and sodium hydride (60% w/w dispersion; 2.3 g; 60 mmol) carefully added. The slurry was allowed to warm to room temperature over 1 hour after which time 1-bromooctane (13 mL; 75 mmol) was added. The mixture was stirred for 5 days, poured onto H2O and extracted with diethylether (2×). The combined organic fractions were dried (MgSO4), filtered and evaporated in vacuo to yield 12.8 g (quantitative yield) of a white solid. Mp. 120° C.

Source