1-Ethynylcyclohexanol

Chemical compound From Wikipedia, the free encyclopedia

1-Ethynylcyclohexanol (ECX) is an alkynyl alcohol derivative which is both a synthetic precursor to, and an active metabolite of the tranquilizer ethinamate, and has similar sedative, anticonvulsant and muscle relaxant effects. It has been sold as a designer drug, first being identified in the UK in March 2012.[1][2][3][4]

CAS Number
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1-Ethynylcyclohexanol
Identifiers
  • 1-ethynylcyclohexan-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.001 Edit this at Wikidata
Chemical and physical data
FormulaC8H12O
Molar mass124.183 g·mol−1
3D model (JSmol)
Melting point30–33 Â°C (86–91 Â°F)
  • C#CC1(CCCCC1)O
  • InChI=1S/C8H12O/c1-2-8(9)6-4-3-5-7-8/h1,9H,3-7H2
  • Key:QYLFHLNFIHBCPR-UHFFFAOYSA-N
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Preparation

Synthesis of 1-ethynylcyclohexanol from cyclohexanone.
Synthesis of 1-ethynylcyclohexanol from cyclohexanone.

1-Ethynylcyclohexanol can be prepared from cyclohexanone by reacting it with sodium acetylide in liquid ammonia, followed by an acidic work-up.[5]

Acetylene also directly reacts with cyclohexanone under basic conditions in liquid ammonia. The base, which is usually sodium hydroxide or potassium hydroxide, deprotonates the acetylene, which then attacks the carbonyl group. The resulting alkoxide is then converted to the alcohol by the proton that was removed from the acetylene.[6]

Industrial synthesis of 1-ethynylcyclohexanol
Industrial synthesis of 1-ethynylcyclohexanol

See also

References

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