Sec.-Octyl alcohol

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

The latter upon decomposition with dilute hydrochloric acid yields laevo sec.-octyl hydrogen phthalate the crystalline brucine salt, when similarly treated, affords the dextro sec.-octyl hydrogen phthalate. These are reerystallised and separately hydrolysed with sodium hydroxide solution to yield pure I- and d-sec.-octyl alcohols ... 

Optically pure I- and d-sec.-octyl alcohols are obtained by distillation in a current of steam of the -octyl hydrogen phthalate and 2 moles of sodium hydroxide in 30 per cent solution. The alcohols are practically insoluble in water and are separated, dried with potassium carbonate and distilled. Each boils at 86 /20 mm. and has a rotation (0)5461-1-11.8°, (a) -1-9.9° ( )546i (0)0 9-9°- The yields of alcohol from the sec.-... 

The yield of sec. -octyl hydrogen phthalate from the crude sec.-octyl alcohol used in this preparation was 61-64 per cent. 

The resolution of sec.-octyl alcohol was first described by Pickard and Kenyon. The method employed by these authors differed from the foregoing in the following respects. The brucine salt of sec.-octyl hydrogen phthalate was crystallized several times from acetone until it reached optical purity and was then decom-... 

Resolution of sec.-octyl alcohol ([Pg.1207]

To obtain optically pure Z- and cZ sec.-octyl alcohols, steam distil the respective esters with 30 per cent, sodium hydroxide solution use the proportions 1 mol of ester to 2 mols of sodium hydroxide. Separate the alcohols from the steam distillate, dry over anhydrous potassium carbonate, and distil under diminished pressure. Both samples boil at 86°/20 mm. (9) and have the following rotations ... 

This is due to methyl n-hexyl.ketone in the original sec.-octyl alcohol it is most easily separated by steam distillation as described. 

---