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Topic: Oxidizing 2-phenylethanol; wich agent to use?  (Read 17708 times)

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Offline jcmtz

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Oxidizing 2-phenylethanol; wich agent to use?
« on: July 03, 2010, 02:50:56 PM »
Hi im having problems oxidizing 2-phenyethanol, to his carboxilic acid, or to his aldehyde. i own a chemical supply, also with a partner we are trying to enter the cleaners industries, and i need several compounds of this carbinol.

since it not dissolves in water, and the oxidation of the KmNO4 its so fast, im having problems.

also, i want to try the jones reagent, or even hot CuO.

any toughts?

Offline Schrödinger

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #1 on: July 03, 2010, 02:59:30 PM »
I don't think KMnO4 is a good idea, since you will get benzoic acid and not 2-phenylethanoic acid.

I think Jones reagent should be OK. I don't think it will disturb the aromatic part.

Please correct me of I am wrong
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Offline jcmtz

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #2 on: July 03, 2010, 03:09:52 PM »
I don't think KMnO4 is a good idea, since you will get benzoic acid and not 2-phenylethanoic acid.

I think Jones reagent should be OK. I don't think it will disturb the aromatic part.

Please correct me of I am wrong


well actually im trying to get phenylacetaldehyde, or ethyl phenylacetate.

2-phenylethanol would give me 2-phenylethanoic acid?



Offline Doc Oc

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #3 on: July 03, 2010, 04:58:48 PM »
The Jones oxidation is fairly acidic and likely to push all the way to the carboxylic acid, which you could esterify if you desire.

However, if phenylacetaldehyde is your desired product then a mild oxidant like IBX or Dess Martin Periodinane will stop at that stage of oxidation.

Offline SVXX

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #4 on: July 04, 2010, 02:02:16 AM »
I dunno if this will work, but you could try a DMSO oxidation to the aldehyde. First do a nucleophilic substitution via PX3 where X =  Cl, Br. Then react this halide with DMSO to form an aldehyde via an oxysulfonium salt intermediate.
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Offline OC pro

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #5 on: July 04, 2010, 07:09:02 AM »
To get to the Aldehyde several methodologies will work:
1) Chromium-based (therefore toxic): PDC, PCC
2) DMSO-based: Swern-Oxidation, Parikh-Doering...
3) IBX (potent explosive), Dess-Martin-Periodinane (expensive)

To get directly from 2-Phenylethanol to Phenylacetic acid:
Jones reagent (again toxic, but works well)

Or stepwise:
Having the aldehyde in hand you can mildly oxidise it with Sodium chlorite.

Offline jcmtz

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #6 on: July 05, 2010, 08:31:31 PM »
ok thanks a lot, any toughs on the hot copper?

i was thinking jones but is highly toxic, and we want to run a green company so lets see.

sodium chlorite? ok and can i oxidize 2-phenylethanol to the aldehyde via sodium chlorite?

Offline jcmtz

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #7 on: July 05, 2010, 08:33:51 PM »
The Jones oxidation is fairly acidic and likely to push all the way to the carboxylic acid, which you could esterify if you desire.

However, if phenylacetaldehyde is your desired product then a mild oxidant like IBX or Dess Martin Periodinane will stop at that stage of oxidation.

can you give me the amount of jones i need or the best way to prepare it?
also how long will the reaction be?

Offline Jorriss

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #8 on: July 06, 2010, 02:47:26 AM »
Woops, made a mistake, editting.

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #9 on: July 06, 2010, 01:28:13 PM »
Here is the original procedure for the Jones oxidation:

http://www.orgsyn.org/orgsyn/default.asp?formgroup=basenpe_form_group&dataaction=db&dbname=orgsyn

I would use twice the equivalents for the conversion of a primary alcohol into an acid.
The reaction works well, I have done it often.

Offline jcmtz

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #10 on: July 06, 2010, 03:56:18 PM »
Here is the original procedure for the Jones oxidation:

http://www.orgsyn.org/orgsyn/default.asp?formgroup=basenpe_form_group&dataaction=db&dbname=orgsyn

I would use twice the equivalents for the conversion of a primary alcohol into an acid.
The reaction works well, I have done it often.


i guess the link was broken, i dont know how much cromate  to add to the H2S04

Offline sjb

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #11 on: July 06, 2010, 04:14:43 PM »

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #12 on: July 07, 2010, 01:21:40 PM »
Perhaps http://www.orgsyn.org/orgsyn/pdfs/CV6P0644.pdf is the link required?

This is the preparation for the so-called Collins reagent which will only give the aldehyde selectively.

Here is the reference: Organic Syntheses, Vol. 45, p. 28 (1965); Coll. Vol. 5, p.310 (1973).

@jcmtz: There is a procedure (which is very mild) giving the acid directly from the alcohol using a combination of catalytic TEMPO/NaOCl (gives the aldehyde) and sodium chlorite (NaClO2 --> further oxidation in situ to the acid).   Organic Syntheses, Vol. 81, p. 195 (2005); Coll. Vol. 11, p.107 (2009).

Both can be found on: www.orgsyn.org

Offline 1907

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #13 on: July 07, 2010, 01:50:20 PM »
odorless corey-kim oxidation may work?

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Re: Oxidizing 2-phenylethanol; wich agent to use?
« Reply #14 on: July 10, 2010, 06:46:19 AM »
Hi im having problems oxidizing 2-phenyethanol, to his carboxilic acid, or to his aldehyde. i own a chemical supply, also with a partner we are trying to enter the cleaners industries, and i need several compounds of this carbinol.

since it not dissolves in water, and the oxidation of the KmNO4 its so fast, im having problems.

also, i want to try the jones reagent, or even hot CuO.

any toughts?
Why not just use bleach/Tempo in dichloromethane, you get the aldehyde exclusively. Remember to stir well.
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