1-Ethynylcyclohexanol

Last updated
1-Ethynylcyclohexanol
1-Ethynylcyclohexanol.svg
Identifiers
  • 1-ethynylcyclohexan-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.001.001 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C8H12O
Molar mass 124.183 g·mol−1
3D model (JSmol)
Melting point 30–33 °C (86–91 °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

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]

Contents

Preparation

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

1-Ethynylcyclohexanol can be prepared from cyclohexanone by the 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 is usually sodium hydroxide or potassium hydroxide. The base deprotonates the acetylene, which then attacks the carbonyl group. The 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.svg
Industrial synthesis of 1-ethynylcyclohexanol

See also

References

  1. ↑ Levina RY, Vinogradova EU (1936). "Action of sodium acetylide on cyclic ketones. I. Synthesis of 1-ethynylcyclohexanol". Zhurnal Prikladnoi Khimii. 9. Sankt-Peterburg, Russian Federation: 1299–1302. ISSN   0044-4618.
  2. ↑ Verkruijsse HD, Graaf WD, Brandsma L (February 1988). "An efficient and quick laboratory scale method for the ethynylation of some aliphatic and cycloaliphatic carbonyl compounds". Synthetic Communications. 18 (2): 131–4. doi:10.1080/00397918808077336.
  3. ↑ Nazarov IN, Kotlyarevskii IL, Ryabchenko VF (1953). "Acetylene derivatives. CLX. Condensation of aldehydes and ketones with acetylene under pressure. New method of synthesis of acetylenic alcohols". Zhurnal Obshchei Khimii. 23: 1900–1904. ISSN   0044-460X.
  4. ↑ "Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA (New drugs in Europe, 2012)" (PDF). Lisbon: EMCDDA. May 2013.
  5. ↑ Saunders JH, Schreiber RS, Jenner EL (1949). "1-ETHYNYLCYCLOHEXANOL" . Organic Syntheses. 29: 47. doi:10.15227/orgsyn.029.0047.
  6. ↑ "Verfahren zur herstellung von acetylenalkoholen". Google Patents. 2003-07-23. Retrieved 2025-11-09.


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