4-Octanol

Beckmann rearrangement of cvc7ohexanone oxime. M.p. 68-70 C, b.p. I39 C/12 mm. On healing it gives polyamides. Used in the manufacture of Nylon[6]. Cyclohexanone oxime is formed from cyclohexane and niirosyl chloride. U.S. production 1978 410 000 tonnes, capryl alcohol See 2-octanol. caiH Uc acid See oclanoic acid. 

RESOLUTION OF sec.-OCTYL ALCOHOL (d/-2-OCTA-NOL) INTO ITS OPTICALLY ACTIVE COMPONENTS (d- AND f-2-OCTANOL)... 

Which of these two opposite stereochemical possibilities operates was determined in experiments with optically active alkyl halides In one such experiment Hughes and Ingold determined that the reaction of 2 bromooctane with hydroxide ion gave 2 octanol having a configuration opposite that of the starting alkyl halide... 

Write the Fischer projection of the (-) 2 octanol formed from it by nucleophilic substitution with inversion of configuration... 

For example the hydrolysis of optically active 2 bromooctane in the absence of added base follows a first order rate law but the resulting 2 octanol is formed with 66% inversion of configuration... 

The same cannot be said about reactions with alkyl halides as substrates The conver Sion of optically active 2 octanol to the corresponding halide does involve a bond to the chirality center and so the optical purity and absolute configuration of the alkyl halide need to be independently established... 

The hydrolysis of sulfonate esters of 2 octanol is stereospecific and proceeds with complete inversion of configuration Write a structural formula that shows the stereochemistry of the 2 octanol formed by hydrolysis of an opti cally pure sample of (S) (+) 1 methylheptyl p toluenesulfonate identify the prod uct as / or S and deduce its specific rotation... 

Rearrangement can occur and the desired alkyl halide is sometimes accompanied by an isomeric halide An example is seen m the case of the secondary alcohol 2 octanol which yields a mixture of 2 and 3 bromooctane... 

Hydrolysis of (R) (—) 2 bromooctane by the 8 2 mechanism yields optically active (S) (-f) 2 octanol The 2 octanol obtained by hydrolysis of racemic 2 bromooctane is not optically active... 

Most manufacturers sell a portion of their alcohol product on the merchant market, retaining a portion for internal use, typically for the manufacture of plasticizers. Sterling Chemicals linear alcohol of 7, 9, and 11 carbons is all used captively. Plasticizer range linear alcohols derived from natural fats and oils, for instance, octanol and decanol derived from coconut oil and 2-octanol derived from castor oil, are of only minor importance in the marketplace. 

Witco Chemical, Dover, Ohio, U.S. 7 2-octanol castor oil... 

Sometimes a skilled peifumei detects a sandalwood-musky note in authentic Bulgarian otto of rose. This note has been identified (11) as the trace iagredient, 7-methoxy-3,7-dimethyl-2-octanol [41890-92-0] (17), which has been commercially available for some time as Ossyrol (trademark of Bush, Boake, Aken Inc). This compound had never before been identified ia nature, but demonstrates how, sometimes, synthetic fragrance chemists can anticipate nature. 

The by-product of this process, pelargonic acid [112-05-0] is also an item of commerce. The usual source of sebacic acid [111-20-6] for nylon-6,10 [9008-66-6] is also from a natural product, ticinoleic acid [141-22-0] (12-hydroxyoleic acid), isolated from castor oil [8001-79-4]. The acid reacts with excess sodium or potassium hydroxide at high temperatures (250—275°C) to produce sebacic acid and 2-octanol [123-96-6] (166) by cleavage at the 9,10-unsaturated position. The manufacture of dodecanedioic acid [693-23-2] for nylon-6,12 begins with the catalytic trimerization of butadiene to make cyclododecatriene [4904-61-4] followed by reduction to cyclododecane [294-62-2] (see Butadiene). The cyclododecane is oxidatively cleaved to dodecanedioic acid in a process similar to that used in adipic acid production. 

Alkali Fusion. Tha alkaU fusion of castor oil using sodium or potassium hydroxide in the presence of catalysts to spHt the ricinoleate molecule, results in two different products depending on reaction conditions (37,38). At lower (180—200°C) reaction temperatures using one mole of alkah, methylhexyl ketone and 10-hydroxydecanoic acid are prepared. The 10-hydroxydecanoic acid is formed in good yield when either castor oil or methyl ricinoleate [141-24-2] is fused in the presence of a high boiling unhindered primary or secondary alcohol such as 1- or 2-octanol. An increase to two moles of alkali/mole ricinoleate and a temperature of 250—275°C produces capryl alcohol [123-96-6] CgH gO, and sebacic acid [111-20-6] C QH gO, (39—41). Sebacic acid is used in the manufacture of nylon-6,10. 

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