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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]
The base used in the original research paper is ammonia and the solvent is water or an alcohol. The reaction was first reported by Carl Andreas Glaser in 1869. [1] [2] He suggested the following process on his way to diphenylbutadiyne: CuCl + PhC 2 H + NH 3 → PhC 2 Cu + NH 4 Cl 4 PhC 2 Cu + O 2 → 2PhC 2 C 2 Ph + 2Cu 2 O
Ethinamate (1-ethynylcyclohexanone carbamate) is synthesized by combining acetylene with cyclohexanone to make 1-ethynylcyclohexanol, and then transforming this into a carbamate by the subsequent reaction with phosgene, and later with ammonia. Some lithium metal or similar is used to make the acetylene react with the cyclohexanone in the first ...
Cyclohexanone is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts: [11]. C 6 H 12 + O 2 → (CH 2) 5 CO + H 2 O. This process forms cyclohexanol as a by-product, and this mixture, called "KA Oil" for ketone-alcohol oil, is the main feedstock for the production of adipic acid.
Several routes exist for the production of cyclohexenone. For the laboratory scale, it can be produced from resorcinol via 1,3-cyclohexanedione. [6] Cyclohexenone is obtained by Birch reduction of anisole followed by acid hydrolysis. It can be obtained from cyclohexanone by α-bromination followed by treatment with base.
Ortho esters are readily hydrolyzed in mild aqueous acid to form esters: . RC(OR ′) 3 + H 2 O → RCO 2 R ′ + 2 R ′ OH. For example, trimethyl orthoformate CH(OCH 3) 3 may be hydrolyzed (under acidic conditions) to methyl formate and methanol; [5] and may be further hydrolyzed (under alkaline conditions) to salts of formic acid and methanol.
The epoxidation can take place either in a homogeneous reaction by peracids [2] or heterogeneous catalysis (e.g. silver and molecular oxygen). [ 3 ] [ 4 ] [ 5 ] In industrial production the heterogeneously catalyzed synthesis is preferred because of better atom economy , a simpler separation of the product and easier recycling of catalyst.
For example, the reaction of acetic anhydride with ethanol yields ethyl acetate: (CH 3 CO) 2 O + CH 3 CH 2 OH → CH 3 CO 2 CH 2 CH 3 + CH 3 COOH. Often a base such as pyridine is added to function as catalyst. In specialized applications, Lewis acidic scandium salts have also proven effective catalysts. [12]