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I’ve written before about MeTHF and though I’d pass along some information I recently came across in the journal Org. Proc Res and Dev.

Solvent Applications of 2-Methyltetrahydrofuran in Organometallic and Biphasic Reactions (abstract)
Aycock, D.F. Org. Process Res. Dev., 11, 1, 156 - 159, 2007, 10.1021/op060155c

Luckily for most, this is in the first issue of the year and is avaiable to everyone. Typically, it is for subscribers only. Free full aticle link Solvent Applications of 2-Methyltetrahydrofuran in Organometallic and Biphasic Reactions (pdf) or an alternate html.

I should point out though that the article is by David F. Aycock who works for Penn Speciality Chemicals and is a primary supplier of MeTHF.

There are several factors that make it such an interesting solvent.

• Unlike THF, it is not completely water miscible and does not readily form emulsions or rag layers.
• Its water solubility is low, 4 g per 100 g water.
• Moderate boiling point of 65.7 °C.
• Available from readily renewable resources (2-furaldehyde from corncobs).
• Forms azetropes with several solvents including water (10.6% water).
• Three times more stable than THF to 5N HCl at 60 °C.
• About the sme tendency as THF to form peroxides.
• Works well for forming Grignard reagents. Can form much more concentrated solutions than is possible with THF.
• Is a suitable replacement for dichloromethane.
• Effective for extracting polar alcohols such as 2-propanol from water. Two extractions with equal volumes extracted 94% of 2-propanol from water. Only 68% was removed using toluene.

On the downside though, this solvent is significantly more expensive than THF. Penn makes the argument though that you don’t have to use an extraction solvent that you must use with THF or that you can make more concentrated solutions of Grignard and so therefore use less solvent.

It is a good article and well worth reading and noting for future use for all chemists.

You can also view other articles in this free issue of Org. Proc Res. & Dev.

Other Resources

Products”>Penn Specialty Chemical Inc. > Products MeTHF
Methyltetrahydrofuran: How to Recover and Dry MeTHF Batchwise (pdf)
Penn Specialty Chemicals Inc.
ChemExper - catalog of chemical suppliers, physical characteristics and search engine (methyltetrahydrofuran)

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