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Phenylacetone (P2P) synthesis from benzaldehyde with butanone

MadHatter

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Even in a scaled-down version.
 

WillD

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I guess what I'm really wondering about is the stochiometry of this reaction. In other write-ups of the bayer-williger I can't seem to find this enormous amounts of GAA. Can somebody help me with the rationale? I'm really close to trying this one out, but the amount of GAA is problematic.
DocXExcess acts as a solvent for the reaction. In terms of accessibility, try to use food vinegar concentrate. But with an excess of water, you need to think about an additional solvent.
 
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MadHatter

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No proble
Excess acts as a solvent for the reaction. In terms of accessibility, try to use food vinegar concentrate.
William DampierNo problem finding 60% concentration in large amounts. Would that suffice, or would I need to dehydrate it first?
 

WillD

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No proble

No problem finding 60% concentration in large amounts. Would that suffice, or would I need to dehydrate it first?
DocXYes, rather an excess of water will make unstable acid, unless it works in situ, but it is unlikely to be in time. You can try distillation or extraction.
 
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WillD

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I guess what I'm really wondering about is the stochiometry of this reaction. In other write-ups of the bayer-williger I can't seem to find this enormous amounts of GAA. Can somebody help me with the rationale? I'm really close to trying this one out, but the amount of GAA is problematic.
DocXThere is also an alternative route. Use hydrogen peroxide and soda ash (sodium carbonate, Na2CO3) for creating sodium percarbonate, a strong oxidizing agent, as is peracetic acid. The reaction will be different, but in the end with the same result.

Edit: rather, baking soda (NaHCO3) can be used to form an epoxide followed by hydrolysis (analog Weitz-Scheffer epoxidation reaction)
 
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ASheSChem

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so, you think we can do 2-Acetoxy-1-phenyl-1-propene with sodium percarbonate ? any idea for the recipe ?
 

Mr.Blanks00

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View attachment 1386
Langkah 1. 3-metil-4-fenil-3-buten-2-satu.
1. Campur 1000 g benzaldehida dan 1000 ml MEK, diaduk dan didinginkan pada 0 *C.
2. Gas HCl digelembungkan secara perlahan melalui campuran selama 1,5 jam.
3. Larutan diaduk selama 1,5 jam pada suhu kamar.
4. Ditambahkan air, dan larutan diekstraksi dengan kloroform, kemudian dicuci dengan larutan natrium bikarbonat dan dikeringkan (Na2SO4).
5. Pelarut dihilangkan di bawah vakum tinggi dan 3-metil-4-fenil-3-buten-2-satu didistilasi di bawah vakum (bp.76-78 *C). Hasil: 1000 gram.

View attachment 1387
Langkah 2. 2-Asetoksi-1-fenil-1-propena.
1. Produk dari Langkah 1, 10.000 ml asam asetat glasial dan 1300 g 50% H2O2 diaduk dan dipanaskan pada suhu 55 *C selama 23 jam.
2. Setelah itu ditambahkan air 10000 ml air.
3. Diekstraksi dengan 5000 ml kloroform.
4. Pelarut dihilangkan di bawah vakum untuk menghasilkan 800 g 2-Asetoksi-1-fenil-1-propena.


View attachment 1388
Langkah 3. 1-fenil-2-propanon.
1. Produk untuk Langkah 2 dan 600 g natrium hidroksida dalam 2500 ml air diaduk pada 50 °C selama 12 jam.
2. Larutan diekstraksi dengan 1000 ml kloroform, dikeringkan (Na2SO4) dan pelarut dihilangkan di bawah vakum. Hasil: 650 gram.
William Dampierhalo, salam kenal, saya peserta baru di sini dari Indonesia, saya ingin bertanya kepada semua ahli kimia, saya membuat p2p dari asam penilasetat dan timbal dan asam glasial dalam botol stainless steel, saya mendapatkan hampir 100% minyak kuning dan merah dan air, saya ingin bertanya apakah minyak kuning itu penilaseton, dan bagaimana cara mencucinya dari kontaminan lain, terima kasih kepada semua ahli kimia yang mau menjawab pertanyaan saya.
 

Mr.Blanks00

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hello, nice to meet you, I'm a new participant here from Indonesia, I want to ask all chemists, I made p2p from penylacetic acid and lead and glacial acid in a stainless steel bottle, I got almost 100% yellow and red oil and water, I want to ask if the yellow oil is penylacetone, and how to wash it from other contaminants, thank you to all chemists who want to answer my question.
 

cokemuffin

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What would you suggest using if chloroform is not available?
 

Jamroz

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I will prepare hcl gas from sulfuric acid and hydrochloric acid, can anyone tell me what amount I need hcl and h2so4? when i know i have added enough gas?
 

UWe9o12jkied91d

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What would you suggest using if chloroform is not available?
cokemuffinI would say DCM, but I might be wrong
You also easily make chloroform by reacting cold 0* C bleach with acetone in stoechiometric amounts with a small 10% ish molar excess of bleach.Nilered has a video.
 

cokemuffin

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I would say DCM, but I might be wrong
You also easily make chloroform by reacting cold 0* C bleach with acetone in stoechiometric amounts with a small 10% ish molar excess of bleach.Nilered has a video.
UWe9o12jkied91dI saw the video, but i'm mainly interested in large scale manufacture, getting 6l chloroform that way is not really cheap and efficient. I'll probably try to further chlorinate DCM to chloroform.
 

TotalSynthesis

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Did anybody try this with caro's acid instead of GAA?
It should get a much better yield, at least i guess i read that somewhere but cant find any paper.

In the Peracetic way, GAA will also be the solvent but when using Caro's acid, i guess our precursor wont be soluble in the H2SO4 H2O2 mixture. Any idea which solvent could be used with Caro's ?
 

MadHatter

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I would be a bit weary mixing a ketone with caros acid ...
 

Drogan39

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View attachment 1386
Step 1. 3-methyl-4-phenyl-3-buten-2-one.
1. Mixed 1000 g benzaldehyde and 1000 ml MEK, stirring and chilled at 0 *C.
2. HCl gas was bubbled slowly through a mixture 1.5 hours.
3. The solution was stirred for 1.5 hours at room temperature.
4. Water was added, and the solution extracted with chloroform, then washed with sodium bicarbonate solution and dried (Na2SO4).
5. Solvent was removed under high vacuum and 3-methyl-4-phenyl-3-buten-2-one was distilled under vacuum (bp.76-78 *C). Yield: 1000 g.

View attachment 1387
View attachment 1386
Step 1. 3-methyl-4-phenyl-3-buten-2-one.
1. Mixed 1000 g benzaldehyde and 1000 ml MEK, stirring and chilled at 0 *C.
2. HCl gas was bubbled slowly through a mixture 1.5 hours.
3. The solution was stirred for 1.5 hours at room temperature.
4. Water was added, and the solution extracted with chloroform, then washed with sodium bicarbonate solution and dried (Na2SO4).
5. Solvent was removed under high vacuum and 3-methyl-4-phenyl-3-buten-2-one was distilled under vacuum (bp.76-78 *C). Yield: 1000 g.

View attachment 1387
Step 2. 2-Acetoxy-1-phenyl-1-propene.
1. Product from Step 1, 10000 ml glacial acetic acid and 1300 g 50% H2O2 was stirring and heated at 55 *C for 23 hours.
2. After this time water added 10000 ml water.
3. Extracted with 5000 ml chloroform.
4. Solvent removed under vaccum to yield 800 g of 2-Acetoxy-1-phenyl-1-propene.


View attachment 1388
Step 3. 1-phenyl-2-propanone.
1. Product for Step 2 and 600 g sodium hydroxide in 2500 ml water was stirred at 50 °C 12 hours.
2. Solution extracted with 1000 ml chloroform, dried (Na2SO4) and the solvent removed under vacuum. Yield: 650 g.
William Dampier
tic acid and 1300 g 50% H2O2 was stirring and heated at 55 *C for 23 hours.
2. After this time water added 10000 ml water.
3. Extracted with 5000 ml chloroform.
4. Solvent removed under vaccum to yield 800 g of 2-Acetoxy-1-phenyl-1-propene.


View attachment 1388
Step 3. 1-phenyl-2-propanone.
1. Product for Step 2 and 600 g sodium hydroxide in 2500 ml water was stirred at 50 °C 12 hours.
2. Solution extracted with 1000 ml chloroform, dried (Na2SO4) and the solvent removed under vacuum. Yield: 650 g.
Sorry dir the Noob question i am Not a chemist.....
From Step 2. 2-Acetoxy-1-phenyl-1-propene.

It is possible to do a electro oxidation?

Like this?

 

Mo0odi

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Methyl ethyl ketone is there an alternative

💝thank you all
 
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Fenster

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Im going to try this synth with dichloro-methane (DCM). I don't see this being an issue only that it will be heavier then water. Any reason to not use readily available DCM and synth Chloroform?
 
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