Perfluoroalkyl acetic acids, RFCH2COOH, 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(F)I, to vinyl acetate, CH2=CHOCOCH3, with formation of the adduct RFCH2CHIOCOCH3. This method is reported as a four-step process that synthesizes perfluoroalkyl acetic acids through the conversion of the adduct into the corresponding ester RFCH2CH2OCOCH3 and alcohol RCH2CH2OH. 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 RFCH2CHO obtained directly in good yields by acid hydrolysis of the primary adduct RFCH2CHIOCOCH3.
A modified procedure for preparing perfluoroalkyl acetic acids from perfluoroalkyl iodides
NAPOLI, MASSIMO;SCIPIONI, ANTONIO;CONTE, LINO;
1994
Abstract
Perfluoroalkyl acetic acids, RFCH2COOH, 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(F)I, to vinyl acetate, CH2=CHOCOCH3, with formation of the adduct RFCH2CHIOCOCH3. This method is reported as a four-step process that synthesizes perfluoroalkyl acetic acids through the conversion of the adduct into the corresponding ester RFCH2CH2OCOCH3 and alcohol RCH2CH2OH. 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 RFCH2CHO obtained directly in good yields by acid hydrolysis of the primary adduct RFCH2CHIOCOCH3.
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