Reaktion #813694

Reaktionsgleichung

Water

trans-4-phenylcyclohexanol

tetrahydrofuran

triethylamine

→

trans-4-phenylcyclohexyl acrylate

Ausbeute 55.1%

Lösungsmittel

acryloyl chloride

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise to the mixture under ice water cooling
2. 2
   Extraktionan organic layer was extracted with ether
3. 3
   WaschenThe ether layer was washed with water
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONThereafter, the solvent was distilled away
6. 6
   SonstigeThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1)
7. 7
   Sonstigerecrystallized from acetone

Vorschrift

First, 2.5 g of trans-4-phenylcyclohexanol, 50 ml of tetrahydrofuran, and 1.8 g of triethylamine were placed in a 100 ml flask. A solution in which 1.7 g of acryloyl chloride was dissolved in 5 ml of benzene was added dropwise to the mixture under ice water cooling. The mixture was allowed to warm to room temperature and stirred for 5 hours. Water was added to the reaction mixture, and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1) and recrystallized from acetone to obtain 1.8 g of trans-4-phenylcyclohexyl acrylate (Y: 55.1%). The compound thus obtained had a purity of 99.7% by GC and 1 spot by TLC. Furthermore, the compound had an m.p. of 67.3° C.

Quelle