Réaction #1746

Équation de réaction

methylene chloride

O-acetyl-4-phenylcyclohexanol

paraformaldehyde

Hydrogen chloride

→

trans-O-Acetyl-4-(4-chloromethylphenyl)-cyclohexanol

Solvants

Conditions de réaction

Traitement

1. 1
   Autrerises to about 30° C.
2. 2
   Autrea substantially homogeneous solution is formed
3. 3
   Autreto react for 15 hours at ambient temperature
4. 4
   AutreThe organic phase is separated off
5. 5
   Extractionthe aqueous phase is extracted with methylene chloride again
6. 6
   LavageThey are washed until neutral,
7. 7
   Autredried
8. 8
   Autreevaporated in vacuo
9. 9
   AutreThe yellow oil remaining is crystallised by trituration with diisopropylether
10. 10
    Autrethe solid product is recrystallised from diisopropylether
11. 11
    AutreWhite crystals are obtained

Mode opératoire

A solution of 24.3 g (0.11 mol) of O-acetyl-4-phenylcyclohexanol in 1300 ml of methylene chloride is combined with 26.0 g (0.86 mol) of paraformaldehyde and 26.0 g (0.19 mol) of zinc chloride. Hydrogen chloride is introduced into this suspension, with stirring, for 2.5 hours, whilst the temperature rises to about 30° C. and a substantially homogeneous solution is formed. The mixture is then allowed to react for 15 hours at ambient temperature and the reaction mixture is then hydrolysed with stirring in about 1.5 litres of ice water. The organic phase is separated off, the aqueous phase is extracted with methylene chloride again and the two organic phases are combined. They are washed until neutral, dried and evaporated in vacuo. The yellow oil remaining is crystallised by trituration with diisopropylether and the solid product is recrystallised from diisopropylether. White crystals are obtained, melting point 87°-89° C.

Source