Reaktion #1337314

Reaktionsgleichung

DCC

(E)-4-(2-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)vinyl)benzoic acid

3,5-difluoro-4-trifluoromethoxyphenol

toluene

→

(E)-3,5-difluoro-4-trifluoromethoxyphenyl 4-(2-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)vinyl)benzoate

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile being cooled with ice in 5 min
2. 2
   SonstigeSeparated crystals
3. 3
   Filtrationwere filtered off
4. 4
   workup.ADDITION80 ml of toluene was added to the filtrate
5. 5
   Waschenwashed with 2N-NaOH five times and with water thrice
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under a reduced pressure
8. 8
   SonstigeThe residue thus obtained

Vorschrift

(E)-4-(2-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)vinyl)benzoic acid in an amount of 1,3 g (3.7 mmol), 0.8 g (3.7 mmol) of 3,5-difluoro-4-trifluoromethoxyphenol, 0.1 g (1.1 mmol) of DMAP, and 30 ml of dichloromethane were mixed. To this mixture was added dropwise 5 ml of solution of 1.0 g (4.8 mmol) of DCC in dichloromethane while being cooled with ice in 5 min, and stirred as it was for 12 hours. Separated crystals were filtered off, and 80 ml of toluene was added to the filtrate, washed with 2N-NaOH five times and with water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure. The residue thus obtained was subjected to silica gel column chromatography (eluent: toluene) to obtain 1.7 g of a crude (E)-3,5-difluoro-4-trifluoromethoxyphenyl 4-(2-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)vinyl)benzoate.

Quelle