A modified procedure for preparing perfluoroalkyl acetic acids from perfluoroalkyl iodides

Article abstract of DOI:10.1016/0022-1139(93)02924-4

Perfluoroalkyl acetic acids, R_FCH2COOH, can be prepared in several ways.Particular attention is here paid to the method starting from the azonitrile-initiated addition of the corresponding perfluoroalkyl iodide, R_FI, to vinyl acetate, CH2=CHOCOCH3, with formation of the adduct R_FCH2CHIOCOCH3.This method is reported as a four-step process that synthesizes perfluoroalkyl acetic acids through the conversion of the adduct into the corresponding ester R_FCH2CH2OCOCH3 and alcohol R_FCH2CH2OH.A simplified procedure consisting of three steps is also suggested: starting from the same reagents, perfluoroalkyl acetic acids can be easily prepared by the oxidation of the corresponding aldehyde R_FCH2CHO obtained directly in good yields by acid hydrolysis of the primary adduct R_FCH2CHIOCOCH3.