Reacción #51271

Ecuación de reacción

2,5-dichloro-2,5-dimethylhexane

dichloromethane

ammonium chloride

dichloromethane

3-bromophenol

→

3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth1-ol

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONis added dropwise
2. 2
   Extracciónextracted with dichloromethane
3. 3
   Lavadothe extract is washed with water
4. 4
   Otrothe organic phase is separated
5. 5
   Secadodried over magnesium sulphate
6. 6
   Otroevaporated
7. 7
   OtroThe residue obtained
8. 8
   Otrois purified by chromatography on a silica column
9. 9
   Lavadoeluted with a mixture
10. 10
    OtroAfter evaporating the solvents, 30.00 g (53%) of the expected compound
11. 11
    Otroare collected in the form of white crystals with a melting point of 93° C.

Procedimiento

13.40 g (100.0 mmol) of ammonium chloride and 100 ml of dichloromethane are introduced into a three-necked flask under an argon atmosphere. A solution composed of 34.60 g (199.0 mmol) of 3-bromophenol, 89.00 g (486.0 mmol) of 2,5-dichloro-2,5-dimethylhexane and 300 ml of dichloromethane is added dropwise. The reaction mixture is stirred for sixteen hours at room temperature. The reaction mixture is poured into water and extracted with dichloromethane, the extract is washed with water and the organic phase is separated by settling, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column eluted with a mixture composed of 80% heptane and 20% dichloromethane. After evaporating the solvents, 30.00 g (53%) of the expected compound are collected in the form of white crystals with a melting point of 93° C.

Fuente