Reacción #362076

Ecuación de reacción

magnesium

6-bromo-1,4-benzodioxane

1,4-cyclohexanedione monoethylene ketal

→

4-(1,4-benzodioxan-6-yl)-4-hydroxycyclohexane

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with saturated NH4Cl
2. 2
   Extracciónextracted with ether
3. 3
   SecadoThe ether extracts were dried with Na2SO4
4. 4
   Otrothe solvent removed in vacuo
5. 5
   workup.ADDITIONAcetone (75 ml) and 1 N HCl (75 ml) were added
6. 6
   workup.STIRRINGthe solution was stirred 18 hr
7. 7
   Otroto give a tan precipitate which
8. 8
   Filtraciónwas filtered
9. 9
   Otroair dried (6.38 g, 59.1%)

Procedimiento

A solution of 1,4-cyclohexanedione monoethylene ketal (7.8 g, 50 mmole) in 50 ml dry THF was added to a of the Grignard reagent prepared from magnesium metal (1.34 g, 55 mmole) and 6-bromo-1,4-benzodioxane (10.75 g, 50 mmole). The mixture was stirred for 16 hr, quenched with saturated NH4Cl and extracted with ether. The ether extracts were dried with Na2SO4 and the solvent removed in vacuo. Acetone (75 ml) and 1 N HCl (75 ml) were added and the solution was stirred 18 hr to give a tan precipitate which was filtered and air dried (6.38 g, 59.1%). This material was used without further purtification.

Fuente