Reaktion #64068

Reaktionsgleichung

hydrochloric acid

ethyl (E)-3-(trans-4-pentylcyclohexyl)acrylate

water

diisobutylaluminium hydride

→

(E)-3-(trans-4-pentylcyclohexyl)allyl alcohol

Ausbeute 88.9%

Lösungsmittel

hexane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter completion of the addition the slightly yellow solution
2. 2
   Sonstigethe organic phase was separated
3. 3
   ExtraktionThe aqueous phase was back-extracted twice with 100 ml of dichloromethane each time
4. 4
   WaschenThe combined organic phases were washed with 500 ml of water, 500 ml of concentrated potassium hydrogen carbonate solution and again with 500 ml of water
5. 5
   Trocknensubsequently dried over magnesium sulphate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   workup.DISTILLATIONDistillation of the residue

Vorschrift

A solution of 13.5 g of ethyl (E)-3-(trans-4-pentylcyclohexyl)acrylate in 100 ml of dichloromethane was treated dropwise at -78° C. and while gassing with nitrogen with a 20% solution of diisobutylaluminium hydride in hexane. After completion of the addition the slightly yellow solution was stirred for a further 1 hour and then treated cautiously with 10 ml of 25% hydrochloric acid. The reaction mixture was poured into 100 ml of water and the organic phase was separated. The aqueous phase was back-extracted twice with 100 ml of dichloromethane each time. The combined organic phases were washed with 500 ml of water, 500 ml of concentrated potassium hydrogen carbonate solution and again with 500 ml of water and subsequently dried over magnesium sulphate, filtered and concentrated. Distillation of the residue gave 10 g of (E)-3-(trans-4-pentylcyclohexyl)allyl alcohol with b.p. 174°-175° C./15 mmHg.

Quelle