Iso propyl iodide

Jso-propyl lactate has been prepared by heating iso-propyl alcohol and lactic acid in a sealed tube at 1700,1 2 and from silver lactate and iso-propyl iodide, together with the iso-propyl ester of a-iso-propoxy-propionic acid.3 Direct esterification of the acid with the alcohol, with sulfuric acid, has failed to give a yield greater than 20 per cent of the theoretical amount, and the product has been less pure. 

The primary iodide is never formed in such reactions. Preparation 123.—iso-Propyl Iodide [2-Iodopropan]. 

Ueda et al. reported a tandem radical addition-cycUzation reaction in aqueous media [184]. This reaction was initiated by single-electron transfer from indium to an alkyl iodide. Fragmentation of the iso-propyl iodide radical anion generated the iso-propyl radical, which triggered the addition/cyclization tandem. Final SET and in situ hydrolysis delivered cyclic sulfonamides in good yield but low stereoselectivity. 

CH3—CH2—CH2I, Normal propyl iodide CH3—CH—CH3, Iso-propyl iodide... 

Ethyl iodide, lodo ethane. Propyl iodide, i-Iodo propane. Iso-propyl iodide, 2-lodo propane. 

As previously pointed out a practical application has been found for isopropyl nitrate. It was originally bebeved 111") that the substance could only be made from iso-propyl iodide and silver nitrate. Direct nitration was found to yield mainly acetone due to the oxidation of the secondary alcoholic group. However a process of continuous nitration of iso-propyl alcohol in the presence of urea has been described by Imperial Chemical Industries patents [36]. isopropyl alcohol and urea were introduced into nitric acid (over 40% HNOj) at its boiling temperature and a current of air stirred and removed unstable products. According to Desscigne (118) the method gave ca. S0% yield. He used nitric acid of over 50% HNO3 at 108-1 lO C. 

Other iV-alkyl-m-toluidines may be prepared by practically the same procedure. The submitters report that -propyl, iso-propyl, and w-butyl derivatives are obtained readily from m-toluidine and the appropriate alkyl iodides (rather than the bromides). In these cases the alkylation is effected by placing the sealed bottle in a beaker of water which is wanned gradually to 70-80° and kept in a warm place until the reaction is completed usually several days are required. 

The question now arises, how may we determine which one of the various formulas, in the case of the five hexanes for instance, is to be assigned to each individual compound of definite physical properties To which one of the butanes, pentanes and hexanes do we assign the straight chain formula or the name normal In the case of the butanes the answer and the reason for it are found in a new synthesis of one of the butanes. We have given one synthesis of the two butanes, viz., from propyl iodide and methyl iodide. As one propyl iodide yields one butane and the other yields the isomeric butane, we know that one of the two isomeric butanes must have the straight chain or normal formula. But we do not know whether the propyl iodide from which the butane boiling at + i is prepared, is really the one possessing the normal or the iso formula. Therefore, it will be seen that the relationship between the isomeric propyl iodides and the isomeric bu-... 

Names of Isomers.—As, we have just stated, the names of the two propyl iodides and of the two butanes may be simply normal and iso. In each group of isomers where only two are possible these two names are sufficient to characterize them as structurally different compounds, and to indicate the structure of each. In the case of pentane, however, three isomers are known, and in that of hexane there are five. In all such cases where there are more than two isomers we must devise other names and these names should be such as to fully express the difference in structure between the isomeric compounds. 

Isopropyl Series. —iso-propyl mercuric hydroxide is formed by treating the halides with moist silver oxide, and has only been obtained in solution. It reacts with acids, giving rise to the following comj ounds chloride needles, M.jDt. 97° C. bromide needles, M.pt. 98° C. iodide plates, M.pt. 125° C. acetate M.pt. 95° C. cyanide, M.pt. 85° C. sulphide, M.jDt. 60° C. 

With minor modifications, this method is suitable for the preparation of ethyl, -propyl, - and fio-butyl and - and iso-amyl iodides with yields above 90 per cent. A somewhat lower deld is obtained in the preparation of sec.-butyl iodide owing to the formation of hydrogen iodide. 

Propyl bromide, 13, 27 iio-Propylbromomalonic acid, 11, 27 T-Propylene glycol, 10, 84 -Propyl iodide, IS, 62 iso-PROPYL lactate, 10, 88 iso-PROPYL THIOCYANATE, 11, 92 Pseudodurene, 10,37 Pyridine, 11, s 12, 20 Pyeomelutic ACID, 10, 90 Pyrrole, 10,113 Pyruvic acid, 10, 114... 

Propyl bromide, 13,21 15, 72 im-Piopylbiomomalonic acid, 11, 21 /-Propylene glycol, 10,84 -Propyl iodide, 13, 62 mo-Propyl lactate, 10,88 ti-Propyl phosphate, 16,10 tt-Piopyl sulfate, 19, 27 -Propyl sulfide, 15, 72 -Propyl sulfite, 19,30 isO-PROPYX THIOCYANATE, 11, 92 ixo-Propyl- t-toluidine, 18, 42 fj-Piopyl- -toluidine, 18, 42 Protocatechualdehyde, 18, 76 Pseudodurene, 10, 37... 

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