Réaction #1593

Équation de réaction

cyclohexylacetylene

formaldehyde

paraformaldehyde

→

3-cyclohexyl-2-propyn-1-ol

Solvants

ether

ether

Conditions de réaction

Traitement

1. 1
   Températurethe reaction mixture was refluxed for 2 hours
2. 2
   Autrewas bubbled into the mixture
3. 3
   TempératureAfter cooling
4. 4
   Autrethe reaction was quenched with saturated ammonium chloride
5. 5
   Extractionextracted with ether (2×100 ml)
6. 6
   LavageThe combined ether extracts were washed with brine
7. 7
   Séchagedried over magnesium sulfate
8. 8
   Autreevaporated
9. 9
   Autreto yield the product which
10. 10
    workup.DISTILLATIONwas distilled under high vacuum at 68°-74° C.
11. 11
    Autreto yield 6.4 g as a colorless liquid

Mode opératoire

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.

Source