[AlphaScent]

Besides mCPBA in DCM, what is the easiest and cheapest way to epoxidize a double bond?

Oxone?

Hydogen peroxide?

I know, weird question.

[discodermolide]

Oxone, not bad. What about making the chlorohydrin ("HOCl") and then treating with base (K₂CO₃)?

[AlphaScent]

See we had this plan in order to just oxidize using mCPBA.  Long story but we decided because of purity we wanted to oxidize and make the epoxide first instead of last.  So we need more material.  2 Kg of mCPBA is like a thousand dollars.  I am like, duh, chemical manufacturing is expensive.  So now at the last minute I am now suppose to come up with a completely new scheme for a 1.5 Kg epoxidation reaction.  I AM LIVID!!!!  Sorry, venting a little...

Attached is the basic premise.   There is also an aldehyde present.  No Bayer-Villager was shown to occur with the mCPBA method.  Why try and do something else??? Makes me angry!!

Disco,

Chloro/bromo hydrin would be performed using an NBS/NCS in DCM, followed by treatment with base to give epoxide.

Doesnt the double bond have to be allylic?  I do a similat reaction using butadiene.  Would it work on the attached molecule?

[AlphaScent]

Sorry, Im flusterd.

Treatment of the olefin with NCS in water will yield the chlorohydrin.

[AlphaScent]

What experience does anyone have with vanadyl acetylacetonate??

[TheUnassuming]

The cheapest would probably be oxone/DMDO. 

[AlphaScent]

Unassuming,

Could you elaborate??  Do you have a reference I could read?

Be awesome if you could!!  No worries if not.  Its my problem.

[AlphaScent]

Ok, so we are just going to do mCPBA for now.  Though it is not the cheapest, it is the most straight forward.

The dimethyldioxirane, though could in theory, is difficult to scale up for my purposes.  I found a organic syntheses procedure for the this type of oxidation (Organic Syntheses, Coll. Vol. 9, p.288 (1998); Vol 74, p.91 (1997).

The DMDO does not get above 0.1 molar.  Far too dilute for large scale work.

The idea of making the halohydrin sounds promising, but with the aldehyde there, the basic conditions will give more headaches than its worth.

In the future, I may look at and experiment with transition metal epoxidation.  Using VO(acac)₂, MoO_2(acac)2

Stressful day...

[TheUnassuming]

So if you need it >1M, DMDO might not work for you as most substrates I've seen are between 0.5-0.1M in the reaction (though trying it on a small scale might not hurt).  I was able to turn up one method that touts itself to be suitable for large scale, though again its not as concentrated as I think  you want: 
Organic Process Research & Development 2002, 6, 405−406

[orgopete]

Benzonitrile, hydrogen peroxide, and potassium carbonate isn't bad either.

[zsinger]

Orgopete's suggestion or the Oxone is how I would proceed.  I would predict slight higher yields from Pete's way.