DL-2-Octanol

Preparation of Hydrogen Phthalate. A mixture of 130 g. (1 mole) of dl-2-octanol and 148 g. (1 mole) of resublimed phthalic anhydride is heated for twelve to fifteen hours in a flask in an oil bath at 110-115° higher temperatures produce a lower yield of dark product, The... 

RESOLUTION OF sec.-OCTYL ALCOHOL (dl-2-OCTA-NOL) INTO ITS OPTICALLY ACTIVE COMPONENTS (d- AND 1-2-OCTANOL)... 

Frankland and Price 17 were the first to attempt the resolution of alcohols (and acids) by fractional crystallization of their solid esters. The isomeric solid esters formed from Z-s-butylcarbinol and di-dibenzoyl-glyceric acid failed to separate on crystallization the corresponding di-alcohol-i-acid ester was liquid. Marckwald and McKenzie 18-19 effected partial resolutions of dl-mandelic acid and related acids with 1-menthol and d-bomeol, and of di-2-octanol with d-tartaric acid, but did not develop a satisfactory method for resolving alcohols. Later investigators, however, have employed the following resolving agents in several more or less successful resolutions of certain alcohols (a) i-menthyl isocyanate, (6) d-camphoric acid, (c) d- or i-mandelic acid, (d) d- or... 

Guaiacyl acetate Heptyl acetate Hexanal 3,4-Hexanedione Hydrocinnamic alcohol Hydroxycitronellal Hydroxycitronellol o-lonone P-lonone Isoamyl acetate Isoamyl alcohol Isoamyl butyrate Isobutyl alcohol Isobutyl propionate dl-Limonene Linalool Linalyl acetate n-Nonyl acetate n-Octanal 2-Octanol... 

With modification, the aforesaid method can sometimes be applied to the resolution of a neutral compound. Such a resolution is accomplished by first converting the neutral compound into a derivative which can form a salt. Resolution of dl-octanol-2 is an example of the application of this modification. The racemic mixture of the alcohol is converted by treatment with phthalic anhydride into the acid phthalate. In the next step the acid phthalate is reacted with the naturally occurring laevorotatory base, brucine. Fractional crystallisation of the resulting mixture of the brucine salts yields the separated salts. Decomposition of the separated salts with hydrochloric acid removes brucine, and the two resulting acid phthalates are then hydrolysed with alkali to get the d- and 1-forms of octanol-2. 

Figure 3.27. Precipitation curves of a PaMS sample with M = 19.6 10 from its cyclohexane solution with octanol as a precipitant. The concentrations arc Cq = 0.033 (/), 0.012 (2), and 0.005 g/dl (. ) (Ramazanov el al., 1982)...

Figure 3.30. Precipitation curves of a PoMS sample with octanol from its cyclohexane. solution (co = 0.0038 g/dl, /o = 4.5 cm) (/) and the restored integral MWl) function (2) (Ramazanov et al., 1983b)...

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