Réaction #9822

Équation de réaction

epibromohydrin

4-nitrocatechol

potassium bicarbonate

→

crystalline title product

Rendement 3.5%

2-Hydroxymethyl-7-nitro-1,4-benzodioxane

Rendement 3.5%

Solvants

DMF

DMF

Conditions de réaction

Traitement

1. 1
   AutreDMF was evaporated
2. 2
   workup.ADDITIONthe residue diluted with 50 ml water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   LavageThe combined organic phases were washed with caustic soda and water
5. 5
   Autre, dried
6. 6
   Autreevaporated
7. 7
   Autrethe supernatant decanted from insoluble parts
8. 8
   TempératureAfter cooling to RT the solution
9. 9
   Autreis again decanted from insoluble oils
10. 10
    workup.WAITleft at RT for 3 d

Mode opératoire

17.6 g 4-nitrocatechol and 11.0 g potassium bicarbonate were stirred in 200 ml DMF at 10° C. 13.99 g epibromohydrin in 10 ml DMF were added dropwise and stirring was continued at 60° C. for another 17 hrs. DMF was evaporated and the residue diluted with 50 ml water and extracted with ethyl acetate. The combined organic phases were washed with caustic soda and water., dried and evaporated. The crude oily product was heated to 90° C. with 200 ml toluene and the supernatant decanted from insoluble parts. After cooling to RT the solution is again decanted from insoluble oils and left at RT for 3 d. A first crop of 0.75 g crystalline title product was obtained. The mother liquor was evaporated and the residue dissolved in 20 dichloromethane at RT. Seeding and chilling to 0° C. yielded another 2.78 g crystalline title product.

Source