Most efficient conversion of HMF to DMF?

[Carvone]

Hello Organic Chemists,

 

I wanted to ask your advice as to what would be the most efficient process to convert hydroxymethylfurfural (HMF) to 2,5-dimethylfuran (DMF).

 

Thanks!!

[hypervalent_iodine]

Hm. I would say catalytic hydrogenation of the carbonyl with Pd, followed by some serious dehydration / hydrogenolysis might do the trick.

 

Edit: I found a paper you might like to take a look at that gives a protocol for pretty much what I just described.

 

http://onlinelibrary.wiley.com/doi/10.1002/anie.201002267/abstract;jsessionid=45767CEB991F7D52EC2D519B45451E1C.d03t02

[Carvone]

Thanks a lot, HI! Can I ask why you named yourself Hypervalent Iodine? Seems so strange to name yourself that. I guess it is a unique catalyst for selective reactions.

[hypervalent_iodine]

I use a certain hyperiodine reagent as a primary component of my PhD project

[Carvone]

Cool. I actually work with iodine in my PhD project but I study starch and use iodine to help elucidate the structure of the starch based on forming a polyiodide complex in the long, straight, unbranched chains of amylose, which gives a vivid blue color, while the highly branched structure of amylopectin turns a red-violet color with iodine due to smaller polyiodide complexes that absorb light at lower wavelengths. I have wondered if this amazing characteristic of iodine has anything to do with its hypervalent nature. Care to share your thoughts on this? Interestingly, iodine is also used in the food industry to titrate different vegetable oils to give a degree of unsaturation due to mono and polyunsaturated fats.