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Topic: synthesis of monosubstituted benzene  (Read 3139 times)

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Offline uri.koffman

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synthesis of monosubstituted benzene
« on: January 29, 2018, 07:45:50 AM »
hello i need some help with the last step of the problem.
my first step was alkylation and the second was nitration but i need to oxidize my nitro group and i struggle with that.

Offline wildfyr

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Re: synthesis of monosubstituted benzene
« Reply #1 on: January 29, 2018, 02:07:46 PM »
Do you mean you have nitroacetophenone and wish to reduce it to aminoacetophenone (the pictured molecule)?

Offline uri.koffman

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Re: synthesis of monosubstituted benzene
« Reply #2 on: January 29, 2018, 02:10:30 PM »
sorry.
yes.
is it ok to do it with pd\c?

Offline sjb

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Re: synthesis of monosubstituted benzene
« Reply #3 on: January 29, 2018, 04:19:47 PM »
sorry.
yes.
is it ok to do it with pd\c?

Possibly - are there issues that you may see?

Offline wildfyr

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Re: synthesis of monosubstituted benzene
« Reply #4 on: January 29, 2018, 04:39:37 PM »
If youre looking for a really mild nitro reduction, I have this one to offer using CaCl2 and iron filings in ethanol/water

SYNLETT 2010, No. 20, pp 3019–3022 DOI: 10.1055/s-0030-1259067

I had reason to find extremely mild condition nitro-reductions to work around an aldehyde group (heck, one is just some quickly and dirtily prepared iron nanoparticles and water) and have more in this vein, though I think Pd/C will work if done judiciously.

Full disclose: I've used Pd/C once in my life, in undergrad lab to do transfer hydrogenation.

Offline kriggy

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Re: synthesis of monosubstituted benzene
« Reply #5 on: February 01, 2018, 02:56:19 AM »
Pd/C is my go-to Nitro reduction method. Mix the cpd with between 0.5-10 molar% of Pd/C in random organic solvent (preferably polar ones like MeOH, EtOAc or acetone, but Ive done it in DCM or THF as well), then remove air, add hydrogen baloon and wait for the yellowish color of nitrogroup to dissapear. Takes anywhere between 10 mins to overnight.

Please dont add dry Pd/C into the reaction flask that has solvent in it, might catch on fire since the catalyst is very reactive. First add the catalyst, then add your compound dissolved.

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