Performic Problem

[Boris_Silicunt]

Swim left a performic running for a couple of hours and came back to find the OH stirrer has broken. The reaction has not finished.  

Can Swim salvage his Isosafrol (250 grams)?

Any help appreciated.

[Rhodium]

Have you or have you not added all the peracid? "Standard" or "Modified" performic?

Anyway, after you have removed all the acids and washed the organic layer with water and bicarbonate, you should be able to separate unreacted isosafrole from any product. If you think you have mostly isosafrole in your mixture, do not subject it to the H₂SO₄ treatment, but rather vacuum distill off the isosafrole using a column, and then only subject the higher-boiling residue (epoxide/glycol/glycol ester) to acid treatment (weigh it and adjust the acid amount accordingly).

[Boris_Silicunt]

Have you or have you not added all the peracid?

about 70% of the acid was added.

"Standard" or "Modified" performic?

buffered performic (modified?)

Anyway, after you have removed all the acids and washed the organic layer with water and bicarbonate, you should be able to separate unreacted isosafrole from any product.

so the Isosafrole will be in the DCM?

[Rhodium]

Yes, everything of interest will be dissolved in the DCM, only the performic acid is water-soluble. If you have added 70% of the performic acid already, I believe that you by now have converted about half of your isosafrole to the oxidation products.

Now simply separate the DCM layer and wash it with 2x100mL water, 2x100mL 10% bicarbonate and 1x100mL brine, then dry the DCM solution over MgSO₄, filter, wash the filter cake with some dry DCM, distill off the DCM (recover for reuse) and subject the residue to vacuum distillation with a column, collecting the isosafrole (recover for reuse). The high-boiling residue (what's left in the distillation flask after no more isosafrole comes over) will consist of oxidation products, which you weigh and heat with a suitable amount of 15% H₂SO₄, then continue as usual to isolate the formed MDP2P.

[Boris_Silicunt]

swim followed your advice on the recovery, but had to leave the reaction in the refrigerator for about 10 days because of work committments.

the reaction had not gone past the light yellow color.

anyway your clean up procedure and after the dcm was removed it gave 224 grams of product.

this was then fracionally distilled to give 217 grams of clear residue that all distilled at the same temperature.

many thanks to rhodium

question

as there was no real fractions should this be all isosafrole?

swim has done a buffered performic before but has not distilled the orange glycol before.

is distilled glycol clear?

the reading of the fractional distillation was similar to isosafrole

many thanks again
 

[MDMA_AcTIvEsTS]

1)I would say that the conversion from safrole to iso-safrole was of a good nature, as if you did not recieve any for-run from the purification via distillation then the conversion may have been good, however one can not speculate as only you can answer.

2) The glycol should be an almost a clear color, and the final MDP2P should be of a yellow nature.

[Rhodium]

The glycol is very viscous, isosafrole is fragrant/non-viscous and MDP2P is yellow. Which one do you have?

[Boris_Silicunt]

>The glycol is very viscous, isosafrole is fragrant/non-viscous and MDP2P is yellow. Which one do you have?

swim tested some of the distillate with a boiling point test and it turned out to be all isosafrole. this seems strange as you stated

>I believe that you by now have converted about half of your isosafrole to the oxidation products.


anyway swim has 217 grams recovered out of 250 grams and is greatful for that. many thanks rhodium.