Formaldehyde → 3-Cyclohexylprop-2-yn-1-ol

HRID 1497

Reaktionsgleichung

Reaktionsgleichung von HRID 1497
[CH:1]1([C:7]#[CH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:9]=[O:10]>CCOCC>[CH:1]1([C:7]#[C:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 712Formaldehyde2×HCID 70263Ethynylcyclohexane

Produkt 1

HCID 3166013-Cyclohexylprop-2-yn-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. customwas bubbled into the mixture
  3. temperatureAfter cooling
  4. customthe reaction was quenched with saturated ammonium chloride
  5. extractionextracted with ether (2×100 ml)
  6. washThe combined ether extracts were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto yield the product which
  10. distillationwas distilled under high vacuum at 68°-74° C.
  11. customto yield 6.4 g as a colorless liquid

Quellen und Nachweise

ORD-Eintrag
ord-1df241b7ff954c60ae215c613fabf759
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726162

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