2-Methyltetrahydrofuran as an Alternative to Dichloromethane in 2-Phase Reactions

Abstract

2-Methyltetrahydrofuran (MTHF) has proven to be a superior solvent to methylene chloride in some 2-phase reactions from process and environmental perspectives.

Key words

2-methyltetrahydrofuran - Schotten-Baumann - solvent - biphasic reaction

References

• 2 Vlasov VM. Russian J. Org. Chem.  1998,  34(9):  1310 
• 3 Jones RA. Aldrichimica Acta  1976,  9(3):  35 

1

A typical procedure is as follows: To a 3-neck, 1 L round bottom flask, add phenol (1.000 equiv, 265.6 mmol, 25.00 g), tetrabutylammonium bromide (0.01500 equiv, 3.985 mmol, 1.285 g), 2-methyltetrahydrofuran, (1.248 mol, 107.5 g, 125.0 mL), o-fluoronitrobenzene (1.000 equiv, 265.6 mmol, 37.48 g), H₂O (100.0 mL), 50% aq NaOH (5.000 equiv, 1.328 mol, 106.2 mL), and heat to a temperature of 75 °C. Stir for 2 h at 75 °C, then cool to a temperature of 20 °C. Split the phases. Concentrate the organic layer to an oil to afford 54.31 g (252.4 mmol, 95.00% of theoretical yield) of 2-nitrophenyl phenyl ether.