Ethyl cyclohexanol

N 4.77% mp 68—9° expl in a flame. Criegee Dietrich (Ref 2) treated 1-ethyl cyclohexanol with 83% hydrogen peroxide and 0.2cm coned sulfuric acid for 14hrs at 0°and purified the Na salt. The peroxide and p-nitrobenzoyl chloride in abs pyridine gave the nitrobenzoate as yellow plates from etber or methanol Refs 1) Beil, not found 2) R. Criegee ... 

One Pot Process for the Preparation of l-[2-Methylamino-(4-Methoxyphenyl)-Ethyl]Cyclohexanol S.P. Chavan etal, US Patent 6,350,912 (February 26, 2002) Council of Scientific and Industrial Research Anti-Depressant Intermediate... 

Alternate Name (lJ ,2S,5J )-5-methyl-2-(l-methyl-l-phenyl-ethyl)cyclohexanol. 

Venlafaxine (l-[2-(Dimethylamino)-l-(4-methoxyphenyl)ethyl]cyclohexanol) is an antidepressant marketed as Effexor . Synthesis of the API is described in U.S. 4,535,186 assigned to American Home Products. Estimate the cost of production of the API. 

Obviously those rules are only general indications and, at the present time, some results seem very strange. For example, 1-ethyl cyclohexanol has a better b.r.p. than 1-methyl cyclohexanol in THF as well as in DME. This order is just reversed for c.g.p. ... 

Internal standard l-[2-(dimethylamino)-l-(2-chlorophenyl)ethyl]cyclohexanol(Wy-45,818) (19.74, 22.38 (enantiomers))... 

Definition Obtained by esterification of ethyl cyclohexanol with propionic acid or anhydride Empirical C11H20O2... 

A soln. of l-cyano-2-methyl-l-(2-pyridyl)cyclopropane in coned. HCl refluxed 0.5 hr., treated with aq. 50%-KOH-soln., refluxed until the organic phase (y-lactone) disappears, the resulting soln. carefully neutralized with 17%-HCl, and gently refluxed 0.5 hr. -> 4-(2-pyridyl)butan-2-ol. Y 52%. - Similarly (Pyrid-2-yl)ethyl]cyclohexanol. Y 90%. F. e. s. C. Piechucki and J. Michalski, Synthesis 1973, 204. 

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