Wo-Amyl alcohol

From synthetic wo-amyl alcohol, t From fermentation iso-amyl alcohol. 

A given alcohol is treated with 25 percent excess of aqueous (48 per cent) hydrobromic acid together with sulfuric acid. The mixture is refluxed in order to convert the alcohol as completely as possible into the corresponding bromide, and the latter is then removed from the reaction mixture by distillation. Slight variations from this procedure depend upon the physical and chemical properties of the alcohol used, or of the bromide formed in the reaction. For example, in the preparations of ethyl and allyl bromides, the reaction mixture is not refluxed because of the volatility of the former compound, and because of the chemical reactivity of the latter in the preparation of wo amyl bromide, too large a proportion of sulfuric acid may produce appreciable decomposition while halides of high molecular weight, because of their low volatility, are separated from the reaction mixture mechanically, instead of by distillation. 

Trimethylethylene dibromide has been obtained by adding bromine to trimethylethylene 1 and to tertiary amyl alcohol.2 Methyl wo-propyl ketone has been prepared by heating trimethylethylene glycol (2-methyl-2,3-dihydroxybutane) with dilute hydrochloric acid,3 by heating trimethylethylene chloro-hydrin (2-methyl-2-hydroxy-3-chlorobutane) in a sealed tube with water,4 by boiling trimethylethylene dibromide with lead oxide (PbO) and water,5 by heating trimethylethylene dibromide with water,6 by the action of iso-propylmagnesium bromide on acetic anhydride,7 and by a variety of other methods not particularly related to the one here described.8... 

The above is a general procedure for preparing trialkyl orthophosphates. Similar yields are obtained for trimethyl phosphate, b.p. 62°/5 mm. triethyl phosphate, b.p. 75-5°/5 mm. tri-n-propyl phosphate, b.p. 107-5°/5 mm. tri-Mo-propyl phosphate, b.p. 83-5°/5 mm. tri-wo-butyl phosphate, b.p. 117°/5-5 mm. and tri- -amyl phosphate, b.p. 167-5°/5 mm. The alkyl phosphates are excellent alkylating agents for primary aromatic amines (see Section IV,41) they can also be ua for alkylating phenols (compare Sections IV,104-105). Trimethyl phosphate also finds application as a methylating agent for aliphatie alcohols (compare Section 111,58). 

F) Preparation and Testing of Candidate Structures. Suitable candidate structures were then examined for relative efficacy in the mobilization of lead from lead-loaded mice. On the basis of previous studies in which we examined the relative ability of many compounds to remove cadmium from its aged deposits in the liver and the kidneys, six vicinal dithiols were selected, which were all monoesters of meso-2,3-dimercaptosuccinic acid. The compounds selected were the mono esters of meso- 2,3-dimercaptosuccinic acid with the following alcohols n-propyl, wo-propyl, n-butyl, wo-butyl, n-amyl, and iso-dmy (Figure 3). The results of experiments comparing these compounds showed that the n-butyl, iso-butyl, n-amyl, and isoamyl monoesters of m j<>-2,3-dimercaptosuccinic acid were the most effective compounds and that all were capable of reducing both kidney and brain lead levels in lead-intoxicated mice (45). The data collected on lead-intoxicated mice treated with the most effective of such compounds are compared with the results obtained with DMSA in Table I. 

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