Sol, what you are referring to (cinnamyl halide + NaH) is the process to prepare the 14-ether.

oh trust me that does'nt work i looked into it found out it's rubish even had a set of lab notes at one time froms someone who tried it and got fuck-all which only confirmed my suspicions.
the only way to oxidize codiene directly to 14-oh codeinone would be MnO2 and not just any will do either it has to be prepared a certain way.

no shit can you provide yeilds?
the chemist i talked to said he could'nt get it to crystallize.
he did'nt do any spectral analysis though.
from what i read you  get  unwanted oxidation at benzylic c-10.
what were your yeilds after you recrystallized it?

you should go straight to 14-oh codeinone esters next time propionyl is about 20 times stronger than morphine.
cinnamyl about 119.
this is very good news you just made my day!
80% yeild that's impressive i wonder why this method is'nt still in use by big pharma?
maybe the trace chromates?
esterifying oxycodone does'nt yeild as potent a product so i think that 7,8 double bond plays a role here in the conformation of that molecule.
i think sodium hypophosphite is just a better hydrogen donor than potassium formate but it still should work using potassium formate.

attached is the reichspatent for oxycodone using sodium dichromate.
anyone spraken duetch?

Jon put up a reference above.  So there's your reference. 

Personally, I made it a point to make my accounting of the synthesis as absolutely detailed as possible.  I also was not lying about the nMR's confirming the steps.  Follow the directions and it works super-easy, especially if you're only going to do the oxidation and then make an ester, which sounds like it's much a better route than making oxycodone or even oxymorphone.

Lemme know which ester sounds most promising with the non-hydrogenated material: cinnamoyl?  propanoyl?

Well, I think I figured out my own question.   14-cinnamoyl greatly increases potency (177x morphine).   But what if one wanted to work with 14-hydroxymorphinone?  I am not sure if there is any lit. on the action or lability of the cinnamoyl group at the 3 position of morphine or codeine.  BUT dibenzoylmophine is known and considered to be around the potency of diacetylmorphine AND 14-benzoylcodeinone is 52x morphine.  So, 3,14-dibenzoylmorphinone sounds like it holds great promise  3,14-dicinnamoylmorphinone could be even better depending on how that cinnamoyl group hydrolizes hopefully after passing the BBB, but even if it hydrolizes too readily, it's not that big of a deal. 

But then I discovered that for this case codeinone vs. morphinone doesn't really matter: "The antinociceptive activity of the cinnamoyloxycodeinones was not significantly greater than that of the morphinones".   So I guess it's time to source out some codeine, oxidize with dichromate and then hit it with cinnamoyl chloride after dissolving the oxycodeinone in pyridine (or maybe Tsathoggua is correct and one required 4-DMAP instead of regular ol' pyridine).  The only advantage to using benzoyl chloride is if you had a mixture of codeine and morphine from one's last harvest of poppies.  (I could REALLY use some help with regard to purification of said harvest!)

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3063885/

What's interesting relating to the naltrexone discussion is that the way they protect the  3-OH is by making the 3-O-(tert-Butyldimethylsilyl), then later remove the group with KF.  But one could also just make the 3-Methoxy and leave it alone because it should have just about the same potency as the 3-OH when one slaps on the 14-phenylpropoxy group.  Personally, I'd need to do further reading to figure out how to only methylate the 3-hydroxy and not the 14, same goes for how to attach that 3-O-(tert-Butyldimethylsilyl) group.  Doing either of these transformations plus making the 14-phenylpropoxy ether has got to be damn easy in order to be able to compete with the dichromate oxidation of codeine (super-easy) followed by acylation with cinnamoyl chloride (also super easy). 

My only real issue is that sadly it seems that naltrexone is more easily available and even cheaper than codeine.  I miss the days when I could buy a gram of codeine (Perduretas) for like $16-18.   

Here's a rough translation of the patent listed above which proves the reaction works!

"1. 20 parts codeine are housed in 80 parts of water, add 25 parts of glacial acetic acid in solution and mixed the cooled liquid with a solution of sodium dichromate in 25 parts of water. The result is an oily precipitate, which after a brief warming is solid and crystalline, the reaction mixture was slowly heated on a water bath under constant stirring to 80 ° , which dissolves the precipitate. Now, interrupt to the warming, due to a subsequent reaction, the temperature rises to about 90 °.

After standing for a short time mixture is cooled and drops off sharply to the newly formed base by addition of chromic acid solution as überschussiger(?) bichromate. The crystallized in the usual bichromate as isolated base from alcohol in leaflets from the decomposition point of 273 ° shows the properties of previously un-described friend of un Oxykodeinons spires(?).

2.  21 parts  Kodeinon are inserted in 80 parts of water, add 25 parts of glacial acetic acid brought fact in solution and then added a solution of 8 parts of sodium dichromate in 25 parts water. The further course of the reaction turns out, as indicated in Example 1. This gives a yield of 8 to 10 parts Oxykodeinon."

Basically, you can get oxycodeinone from codeine or from codeinone.   

no you can make the ester and selectively de-esterify at c-3 with room temp 4% h2so4 or potassium carbonate see the supplementary here.
this example uses the 3-o protected substrate allow me to find the other examples

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3063885/

The ether (2a) in vivo gave a full response in a battery of thermal antinociceptive assays with potency up to 400 times greater than morphine.7 In comparison the cinnamoyl ester has much more modest in vitro and in vivo MOR agonist activity. It must be assumed that the relative conformational restraint of the ?,?-unsaturated cinnamoyl ester prevents an optimum interaction with MOR in the preferred agonist conformation

The 14-O-cinnamoyl esters of naltrexone have predominant opioid receptor antagonist activity both in vitro and in vivo. In this regard they are similar to the equivalent 14-N-cinnamoylamino derivatives, but the latter are more potent antagonists of longer duration. Additionally the naltrexone esters (6) have similar in vivo and in vitro MOR efficacy to the corresponding codeinones (7) whereas the codeinone amides (4) have substantially higher MOR efficacy than the morphinones (5). These differences are less significant than the difference between 14-cinnamoylnaltrexone (6a) and 14-O-phenylpropylnaltrexone (2a). The greater side chain conformational freedom of the latter allows it to display very high potency in vivo MOR agonist activity.

also 6-beta naltrexamines are kappa agonists with the meta nitro cinnamyl naltrexamine being primarily mu agonist.
for structure activity study

http://www.ncbi.nlm.nih.gov/pubmed/19253970

i used to take black tar and just treat it with activated c.
it got it to acceptable purity if i wanted it purer i would wash it with chloroform.