Work

2,2,6,6-Tetramethyloxane as an Alternative Hindered Ether Solvent for Organic Synthesis

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide A new hindered ether solvent, namely, 2,2,6,6-tetramethyloxane, has been successfully synthesized in excellent yields (90% from 2,6-dimethyl-2,6-heptanediol and 80% from 2,6-dimethyl-5-hepten-2-ol). The physical and solvation properties of 2,2,6,6-tetramethyloxane were evaluated, which indicated its potential to replace hydrocarbon solvents and also that it imparts strong hydrogen-bond-accepting ability. VEGA models (SARpy, KNN, ISS, and CAESAR), the lazy structure–activity relationship model ( Salmonella typhimurium ), and the Toxicity Estimation Software Tool indicated this solvent to be nonmutagenic. The application of 2,2,6,6-tetramethyloxane in model organic reactions including the Biginelli reaction, glucose conversion to 5-hydroxymethylfurfural, and the Sonogashira reaction, importantly, validates the nonpolar nature of this solvent and exhibits its potential as an alternative solvent to hazardous hydrocarbon solvents (including toluene).

Source: ACS Sustainable Chemistry & Engineering

DOI: 10.1021/acssuschemeng.4c09195

Authors: Suwiwat Sangon, Nontipa Supanchaiyamat, James Sherwood, Duncan J. Macquarrie, Andrew J. Hunt

Institutions: Khon Kaen University, University of York

Language: English

Topic: Chemistry and Chemical Engineering

Subfield: Environmental Chemistry

Field: Environmental Science

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Institute for the Promotion of Teaching Science and Technology, National Research Council of Thailand, Ministry of Higher Education, Science, Research and Innovation, Thailand, Materials Chemistry Research Center, Khon Kaen University