Solvent-free tetrahydropyranylation of alcohols catalyzed by amine methanesulfonates

Abstract

A comparative study of tetrahydropyranylation of alcohols under various solvents or solvent-free conditions using different amine methanesulfonates as catalysts shows that tetrahydropyranyl ethers of alcohols are obtained under solvent-free conditions in good yields using catalytic amounts of triethylenediamine methanesulfonate, 1,6-hexanediamine methanesulfonate, diethylenetriamine methanesulfonate and pyridine methanesulfonate, respectively. The reaction occurs readily in short times at room temperature catalyzed by these catalysts, especially triethylenediamine methanesulfonate. Some of the major advantages of this procedure are that the catalysts are environmentally friendly, highly effective, and easy to prepare and handle. The reaction is also clean and needs no solvent, and the work-up is very simple.

Designing Thermally Stable Organocatalysts for Poly(ethylene terephthalate) Synthesis: Toward a One-Pot, Closed-Loop Chemical Recycling System for PET

“…The solid was collected, washed with acetone, and dried under vacuum at room temperature overnight (1.90 g, 87%). Characterization is consistent with that reported previously …”

“…DABCO:MSA (1:2) salt was synthesized as reported previously . DABCO (0.808 g, 7.2 mmol), acetone (10 mL), and MSA (1.45 g, 0.982 mL, 15.1 mmol) were mixed in a round-bottom flask.…”

Synthesis of Polyacrylonitrile Fiber‐Supported Poly(ammonium methanesulfonate)s as Active and Recyclable Heterogeneous Brønsted Acid Catalysts

“…Moreover, the amine methanesulfonates acting as the Brønsted acid catalyst have been verified in the tetrahydropyranylation of alcohols. [11] Based on the above and in continuation of our interest in green chemistry, and in the course of our investigations into applications of synthons as new supports for novel Brønsted acid catalysts, [12] in the present study, we adequately demonstrate that the easily synthesized, PANF-supported poly(ammonium methanesulfonate)s (PANF-PAMSA) function as supported acid catalysts to mediate Biginelli reactions in ethanol, Pechmann condensations in toluene, Friedel-Crafts alkylation reactions of indoles in water and the conversion of fructose to 5-hydroxymethylfurfural (HMF) in DMSO and mixed-aqueous system (Scheme 1), providing an efficient and recyclable heterogeneous Brønsted acid catalyst for organic synthesis.…”

Relationship between bridged groups and antioxidant activity for aliphatic diamine bridged hindered phenol in polyolefins

“…Antioxidant 1098 was purchased from Ciba Specialty Chemicals (Shanghai, China). 3‐(3,5‐Di‐ tert ‐butyl‐4‐hydroxy‐phenyl)‐propionyl chloride (3,5‐propionyl chloride) was synthesized in our laboratory . Unstabilized PP and LLDPE were kindly supplied by Daqing Chemical Engineering Research Center (Daqing, China) and were stored in the dark.…”