Octanol 2-Octen

Korgel and coworkers [378-380] have reported a method to prepare Si nanocrystals at high temperatures in supercritical hexane and cyclohexane. The Si nanoparticles were capped with octanol, octene, and octanethiol. 

Chlorooctane (14 9 g, 0 I mol), potassium fluoride dihydrate (47 g, 0 5 mol), hexadecyltributylphosphonium bromide (5 1 g, 0 01 mol), and water (30 mL) are mixed in an autoclave equipped with a magnetic stirrer and heated to 160 °C (bath temperature) for 7 h After this time gas-liquid chromatographic analysis (10% Carbowax 20M on Chromosorb) shows a 95% conversion to a mixture of 1-fluorooctane (82%), octenes (6%), and 1-octanol (7%) The organic layer is separated, washed with water, washed with concentrated sulfuric acid, washed once again with water, dried over calcium chloride, and distilled to give 10 g (77%) of ] -fluorooctane... 

The product is 2,7-octadien-l-oI which can be dehydrogenated/hydrogenated internally to give 7-octenal, which can be hydroformylated to the dialdehyde, nonadialdehyde, and then hydrogenated to nonadiol. The initial product can be hydrogenated to 1-octanol the dialdehyde can be oxidized to the diacid. The catalyst used is Pd modified with the Li salt of monosulphonated triphenylphosphine. 

The reaction product of telomerization is 2,7-octadiene-l-ol. In subsequent steps this dienol may be converted to 1-octanol by hydrogenation or hydrogenated/dehydrogenated to 1-octenal. This unsaturated aldehyde again can be hydroformylated to yield nonadialdehyde and then hydrogenated to nonadiol. 

Scheme 2 Two industrial processes involving a palladium-catalyzed telomerization step the production of 1-octanol by Kuraray (left) and 1-octene by Dow Chemical (right)...

Alcohols Butanol, Pentanol, Heptanol Octanol. l-Octen-3-oI CORC ++ Octanol (Octa) (RV = 0.960)... 

As mentioned earlier, two side reactions are present Octene is formed to a low extent (<2 %), and this might occur by dehydration of the 1-octanol or by splitting of an ester. Due to the small amounts, neither the mechanism of octene formation was further investigated, nor the principally possible isomerization of octene and subsequent formation of secondary esters or ethers. 

Pfifferling Cantharellus cibarius 1 -octen-3-ol 1-Octen-3-ol, 3-octanol, 2-heptanol, benzaldehyde 177... 

Th02 shows catalytic behavior similar to Z1O2. The selectivity of Th02 (prepared by hydrolysis of the nitrate) for the formation of 1-octene from 2-octanol is very high (99%). ... 

In fact, whenever the primary carbonium ion is formed from the proper substrate, ring expansion is observed this is the case in the acid-catalyzed dehydration of 2-hydroxymethylbicyclo[2.2.1]heptane (23), producing a mixture of 2.5% methylenebicyclo[2.2.1]heptane (7), 87% bicyclo[3.2.1]-2-octene (5), and 10% bicyclo[3.3.0]-2-octene (6) and in the nitrous acid deamination of 2-aminomethylbicyclo[2.2.1]-heptane to bicyclo[3.2.1]- and bicyclo[2.2.2]octanols 30). 

The passage from bicyclo[2.2.2]octane structures to the isomeric bicyclo[3.2.1]octanes is irreversible for all practical purposes in the CsHiz and C9H14 series (it was not investigated in the CioHie series) and this conclusion is substantiated by other facts the acid-catalyzed dehydration of 2-methylbicyclo[3.2.1]-2-octanols and 3-methylbicyclo-[3.2.1]-3-octanols gives small quantities of methylbicyclo[2.2.2]octenes 30), while the acid-catalyzed hydration of bicyclo[2.2.2]-2-octene forms the bicyclo[3.2.1]-2-octanol 27) the nitrous acid deamination of 2-aminobicyclo[2.2.2]-5-octene goes to bicyclo[3.2.1]octenols 31) and the solvolysis of bicyclo[2.2.2]-5-octen-2-ol esters to bicyclo[3.2.1]octenols 32). 

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