Iodoethyl alcohol

Gabriel, Steizner, Ber., 1895, 28, 2929. Ethylene iodohydrin (2-Iodoethyl alcohol, 2-iodo-l-hydroxyethane)... 

Chloroethyl)polystyrenes and (iodoethyl)polystyrenes are each prepared from the alcohol by common reagents in a single step without complications, but one-pot procedures fail to produce completely pure bromide, which must be prepared from the tosylate by assisted halide exchange (57). The preparation of (toluenesulfonyloxyethyl)polystyrene itself, if performed in ice-cold pyridine as for the free analogue (64, 65), required a week to complete (67) if quaternary ammonium and other side-products (68) are to be avoided. In contrast, with non-nucleophilic diisopropylamine (69) as acid acceptor instead of pyridine, (hydroxyethyl)polystyrene and toluene-sulfonyl chloride need only be refluxed in carbon tetrachloride for a few hours to give the desired tosic ester as sole product in quantitative yield (57). 

The acetoxy group of 9-(l-acetoxyethyl)carbazole is easily displaced with alcohols. Easy displacement of a similarly situated halogen can be achieved, as has been noted before (see Section II,C,2) thus methanol converts 9-(l-chloro-2-iodoethyl)carbazole to 9-(2-iodo-l-methoxyethyI) car-bazole. Elimination of acetic acid or ethanol by strongly heating 9-(l-acetoxyalkyl)- or 9-(l-ethoxyalkyl)carbazoles gives 9-vinylcarbazoles. In the absence of acid, ( )-alkenes are produced, but acid catalysis leads to a mixture of E and Z isomers. Acetyl chloride in pyridine also effects ethanol elimination. ... 

Iodoethyl benzoate has been obtained by the action of alcoholic sodium iodide on 2-chloroethyl benzoate. ... 

Denmark has also shown that the uncatalyzed ethylidenation of cinnamyl alcohol using bis(l-iodoethyl)zinc produced the cyclopropanes 13 and 14 in a 71 29 ratio (Scheme 7) [19]. This ratio decreased to 65 35 (13 14) in the presence of the disulfonamide 11. Both compounds had modest enantiomeric excesses. 

Esterification.—iVAWW -Tetramethylchloroformamidinium chloride, which is readily prepared from iVAWW -tetramethylurea and oxalyl chloride, is an efficient reagent for the esterification of carboxylic acids with alcohols yields of between 66 and 97% are obtained, and the method has also been applied to macrolide synthesis. A modified one-pot procedure for the esterification of carboxylic acids, using phenyl dichlorophosphate-dimethylformamide complex, has appeared. A simple method of activation of carboxylic acids, using methanesulphonyl chloride and triethylamine followed by addition of the alcohol and 4-dimethylaminopyridine, leads to esters in 57— 96% yield for thirteen examples. 0-Methylcaprolactim reacts with carboxylic acids to give methyl esters in 73—91 % yield for seven examples and 2-iodoethyl esters are prepared from acyl chlorides, ethylene oxide, and sodium iodide. Transesterification, catalysed by titanium(iv) alkoxides, provides an effective method for synthesis of esters. Diethyl trichloromethylphosphonate reacts with carboxylic acids to give ethyl esters via transesterification, in 52 to 98 % yield. ... 

---