Ionic Liquids Promoted the C-Acylation of Acetals in Solvent-free Conditions

• Published in: Catalysis letters Vol. 130; no. 1-2; pp. 93 - 99
• Main Authors: Martins, Marcos A. P, Guarda, Emerson A, Frizzo, Clarissa P, Moreira, Dayse N, Marzari, Mara R. B, Zanatta, Nilo, Bonacorso, Helio G
• Format: Journal Article
• Language: English
• Published: Boston Boston : Springer US 01-06-2009; Springer US; Springer; Springer Nature B.V
• Subjects: Acetals; Acylation; Anhydrides; Catalysis; Chemistry; Chemistry and Materials Science; Exact sciences and technology; General and physical chemistry; Industrial Chemistry/Chemical Engineering; Ionic liquids; Ions; Organometallic Chemistry; Physical Chemistry; Reaction time; Solvents; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Ionic liquids; C-Acylation; Halogen compounds; Enones; Nitrogen heterocycle; Hexafluophosphates; Tetrafluoborates; Ionic liquid; Acetal; Pyridine; Synthesis; Solvent free reaction; Six membered ring; Chlorides; Halogen compound; Reaction time; pH; Enone; Acylation
• ISSN: 1011-372X; 1572-879X
• DOI: 10.1007/s10562-009-9873-6

The synthesis of a series of fourteen 4-alkoxy-1,1,1-trihalo-3-alken-2-ones (2,3) [CX₃COC(R²)=C(R¹)OMe, where X = Cl, F; R¹/R² = Me/H, Bu/H, i-Bu/H, Ph/H, Thien-2-yl/H, -(CH₂)₄-, -CH(CH₂)₄CH(CH₂)₂-] from the acylation reactions of acetals (1) with trichloroacetyl chloride or trifluoroacetic anhydride in the presence of equimolar amounts of pyridine and imidazolium based ionic liquid ([BMIM][BF₄] or [BMIM][PF₆]) is reported. The reaction time, yields and IL recyclation are also investigated and this method showed advantages over the methods described in the literature.