Synthesis Route for Diol to Oxalane

[dkhoo]

I have a need to convert the following compound but I could not figure out the experimental procedure. I would appreciate for any advise.

 

 

 

 

 

 

 

What are the reagents, conditions and steps required?

 

1. Acetone .

2. What else?

Edited December 1, 2011 by dkhoo

[hypervalent_iodine]

Alright, the first question you should ask yourself is what find of functional group is in your product? You identified the key reagent to making it, acetone, but you're missing one other thing needed to make this particular functional group. It may help you to look at the mechanism.

Edited December 1, 2011 by hypervalent_iodine

[mississippichem]

Think mechanistically. Does something need to be protonated or deprotonated in order to get your nucleophile to bite the carbonyl?

[william santos]

Hello all!

 

You must use CH3COCH3 + Ethylene glycol, so you will got it.

It's a reaction of cetone reduction to Oxolane.

 

1,3 Dioxolane - Dimethyl

 

Sry about my bad english. ^^

 

I'm sry, is a reaction of oxidation. Cuz if you reduce a cetone you will got a secundary alcohol.

Edited December 2, 2011 by william santos

[hypervalent_iodine]

William, both the OP and your post are missing one critical reagent in your synthesis.

 

Since I assume the need for this answer has expired, I will give you a big hint by telling you that the compound is an acetal. What is required for acetal formation to occur?

Edited December 2, 2011 by hypervalent_iodine

[william santos]

Aldehyde + alcohol = Acetal. I think this is not a reaction with aldehydes. I can draw the mechanism if you want.

Edited December 2, 2011 by william santos

[hypervalent_iodine]

You're still missing something (and the compound in the OP is an acetal, by the way). Draw the mechanism and you'll probably work it out. A

Edited December 2, 2011 by hypervalent_iodine

[dkhoo]

I know the mechanism. I just need the condition at which this reaction can be carried out as I am carrying it out and not just doing the theory part

[hypervalent_iodine]

If you know the mechanism, it should be fairly apparent what you're missing to drive the reaction. Hint: the addition of this is not needed for hemiacetal formation, but it is required for acetals.

[Horza2002]

You do need to missing bit to make a hemiacetal as well though...its the catalyst

[Suxamethonium]

So I'm confused as to whether you understand the missing reagent?

 

As others were trying to point out, the reagent can be determined mechanistically. You have suggested you know the mechanism, which I beleive as it is easily aquired from a google search, so I will just tell you the reagent you are missing.

 

You need an acid catalyst. In literature I have noted that TsOH is used, however I feel comfortable assuming that other acids (e.g. HCl) would be effective. TsOH is probably used in literature because of its solubility in non-polar solvents like benzene.