Caproates

Small quantities of esters (in the above example n-hexyl n-caproate CH3(CHj)3COO(CH2)jCH3) are simultaneously formed. This is an excellent method for the preparation of aldehydes. 

If tile high boiling residue is transferred to a small Claisen flask and distilled, some n-hexj l alcohol passes over first, followed by n-hexyl n-caproate (2 g.) at 240-250° (mainly 245°). 

It is essential to remove the alcohol completely, otherwise some ethyl n-caproate, b.p. 168°, is formed which will contaminate the final product. 

M-Hexyl alcohol has been prepared by the reduction of ethyl caproate by means of sodium and absolute alcohoB alone or in anhydrous ammonia solution by the reduction of -caproamide by means of sodium and absolute alcohol by the reduction of -caproaldehyde by means of sodium amalgam in dilute sulfuric acid and by means of living yeast, It has also been produced by the action of nitrous acid upon w-hexylamine by the action of sodium upon a mixture of ethyl alcohol and M-butyl alcohol ... 

Sodium decanoate (sodium caproate) [1002-62-6] M 194.2. Neutralised by adding a slight excess of the free acid, recovering the excess acid by Et20 extraction. The salt is crystd from solution by adding pure acetone, repeating the steps several times, then dried in an oven at ca 110° [Chaudhury and Awuwallia Trans Faraday Soc 77 3119 1981]. 

In a modification of this scheme, hydroxypregnenolone is first acetylated under mild conditions to the 3-acetate and then under forcing conditions with caproic anhydride to give the acetate-caproate (122). Ester interchange with methanol removes the acetate at 3 Oppenauer oxidation affords hydroxyprogesterone caproate (124). ... 

Methylsulfinyl -pentyl ketone is prepared by the reaction of the reagent (0.1 mole) and 7.2 g (0.05 mole) of ethyl caproate yielding the crude product as a pasty crystalline mass. The material is dissolved in hot isopropyl ether (20 ml), petroleum ether (30 ml) is added, and the solution cooled to -15°. Filtration yields approx. 6 g of white plates, mp 40-44°. Recrystallization from isopropyl ether affords pure product, mp 45-47°. 

By oxidation in 100 cc of absolute toluol with 425 cc of cyclohexanone and 155 cc of a 20% aluminum isopropylate solution in absolute toluol and after repeated crystallizations from isopropyl ether or methanol, 24 grams of pure 17o-oxyprogesterone-17-caproate is obtained, MP 119° to 121°C (dense needles). 

Hydroxyprogesterone caproate Cyclohexylacetone Droprenilamine HCl Propylhexedrine Cyclohexylamine Clorexolone Cyclamate calcium 1 -Cyclohexylamino-2-propanol Hexylcaine HCl Cyclohexyl bromide Cetiedll... 

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