Reaktion #1593

Reaktionsgleichung

cyclohexylacetylene

formaldehyde

paraformaldehyde

→

3-cyclohexyl-2-propyn-1-ol

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was refluxed for 2 hours
2. 2
   Sonstigewas bubbled into the mixture
3. 3
   TemperaturAfter cooling
4. 4
   Sonstigethe reaction was quenched with saturated ammonium chloride
5. 5
   Extraktionextracted with ether (2×100 ml)
6. 6
   WaschenThe combined ether extracts were washed with brine
7. 7
   Trocknendried over magnesium sulfate
8. 8
   Sonstigeevaporated
9. 9
   Sonstigeto yield the product which
10. 10
    workup.DISTILLATIONwas distilled under high vacuum at 68°-74° C.
11. 11
    Sonstigeto yield 6.4 g as a colorless liquid

Vorschrift

To a solution of ethyl magesium bromide (prepared from 2.5 g of magnesium turning and 11.3 g of bromoethane) in ether was added dropwise a solution of 10.2 g of cyclohexylacetylene in ether and the reaction mixture was refluxed for 2 hours. The reaction mixture was cooled to ambient temperature and anhydrous formaldehyde (prepared from the thermal decomposition of 50 g of paraformaldehyde for 20 minutes) was bubbled into the mixture. After cooling, the reaction was quenched with saturated ammonium chloride and extracted with ether (2×100 ml). The combined ether extracts were washed with brine, dried over magnesium sulfate and evaporated to yield the product which was distilled under high vacuum at 68°-74° C. to yield 6.4 g as a colorless liquid.

Quelle