Reacción #1463477

Ecuación de reacción

water

trans-4-(4-fluoro-cyclohex-3-enyl)cyclohexanecarbaldehyde

2-propyl-propane-l,3-diol

p-toluenesulphonic acid

→

trans-2-[trans-4-(4-fluoro-cyclohex-3-enyl)cyclohexyl]-5-propyl-[1,3]-dioxane

Rendimiento 47.4%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 1 hour in an apparatus which
2. 2
   TemperaturaAfter cooling the reaction solution
3. 3
   Otrowas partitioned in water/ether
4. 4
   LavadoThe organic phase was washed twice with water
5. 5
   ExtracciónThe aqueous phases were extracted twice with ether
6. 6
   Secadodried over magnesium sulphate
7. 7
   Filtraciónfiltered
8. 8
   Otrothe filtrate was evaporated
9. 9
   OtroThe crude product was recrystallized several times from ethanol/1% ethyl acetate

Procedimiento

500 mg of trans-4-(4-fluoro-cyclohex-3-enyl)cyclohexanecarbaldehyde, 310 mg of 2-propyl-propane-l,3-diol and 50 mg of p-toluenesulphonic acid in 8 ml of toluene were boiled at reflux for 1 hour in an apparatus which was gassed with nitrogen and which was fitted with a water separator. After cooling the reaction solution was partitioned in water/ether. The organic phase was washed twice with water. The aqueous phases were extracted twice with ether. The organic phases were combined, dried over magnesium sulphate, filtered and the filtrate was evaporated. The crude product was recrystallized several times from ethanol/1% ethyl acetate and gave 350 mg of trans-2-[trans-4-(4-fluoro-cyclohex-3-enyl)cyclohexyl]-5-propyl-[1,3]-dioxane, m.p. (C-N)<room temperature; S-N 104° C., c1.p. (N-I) 118.3° C.;

Fuente