Reaktion #1463477

Reaktionsgleichung

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

Ausbeute 47.4%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 1 hour in an apparatus which
2. 2
   TemperaturAfter cooling the reaction solution
3. 3
   Sonstigewas partitioned in water/ether
4. 4
   WaschenThe organic phase was washed twice with water
5. 5
   ExtraktionThe aqueous phases were extracted twice with ether
6. 6
   Trocknendried over magnesium sulphate
7. 7
   Filtrationfiltered
8. 8
   Sonstigethe filtrate was evaporated
9. 9
   SonstigeThe crude product was recrystallized several times from ethanol/1% ethyl acetate

Vorschrift

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.;

Quelle