TITLE:
Novel Synthetic Method for the Vilsmeier-Haack Reagent and Green Routes to Acid Chlorides, Alkyl Formates, and Alkyl Chlorides
AUTHORS:
Yoshikazu Kimura, Daisuke Matsuura
KEYWORDS:
Phthaloyl Dichloride; Vilsmeier-Haack Reagent; Acid Chlorides; Alkyl Formates; Alkyl Chlorides
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.3 No.3A,
November
5,
2013
ABSTRACT: An environmentally benign and practical preparation method for the Vilsmeier-Haack reagent (VH) has been developed by using phthaloyl dichloride with DMF in toluene or 2-chlorotoluene. Phthalic anhydride as the byproduct was recovered in high yield by simple filtration. Some aromatic acids have been transformed into the corresponding acid chlorides in good yields by employing the isolated VH. Treatment of primary or secondary alcohols with VH gave alkyl formates or alkyl chlorides by depending on the reaction conditions.