weaver - 5-12-2007 at 18:57
Have been attempting to perform this reaction using hydrogen peroxide without much success. Only info I've found so far was for ring substituted
phenylacetaldehydes using 1.7 molar excess of H2O2 in an acetic acid/water solvent which was unsuccessful. Does anyone have any info/experience
relating specifically to this reaction as it would be very helpful to me.
chemrox - 5-12-2007 at 22:13
How about oxidation with MnO4 or Cr2O7?
The_Davster - 5-12-2007 at 22:29
Would not permanganate cleave the C-C bond resulting in benzoic acid?
Many oxidation reactions are available in a brochure from Acros...
It is absolutely an awesome summary.
http://www.acros.com/_Rainbow/pdf/oxidation_brochure_MANGA.p...
Dichromate is likely more suitable here than permanganate for your desired reaction.
[Edited on 5-12-2007 by The_Davster]
chemrox - 5-12-2007 at 23:14
I think the D_ is right. Awsome site _D, thanks.
Nicodem - 7-12-2007 at 10:28
For oxidations of phenylacetaldehyde to phenylacetic acid see Tetrahedron 54 (1998) 401-410 and Synthesis (1993) 295-297.
solo - 7-12-2007 at 11:23
Reference Information
Oxidation of aldehydes with Oxone® in aqueous acetone
Kevin S. Webb and Stephen J. Ruszkay
Tetrahedron Volume 54, Issues 3-4, 15 January 1998, Pages 401-410
[Edited on 7-12-2007 by solo]
Attachment: Oxidation of aldehydes with Oxone® in aqueous acetone.pdf (629kB)
This file has been downloaded 2067 times
solo - 7-12-2007 at 16:37
Reference Information
The Oxidation of Aromatic Aldehydes to Carboxylic Acids Using Hydrogen Peroxide in Formic Acid
Robert H. Dodd*, Mireille Le Hyaric
Synthesis 1993: 295-297
Attachment: The Oxidation of Aromatic Aldehydes to Carboxylic Acids Using Hydrogen Peroxide in Formic Acid.pdf (227kB)
This file has been downloaded 4273 times
Mush - 18-7-2009 at 03:07
Hi Everyone! I am looking for an article: J. Chem. Soc., Trans. (1921) 119, 1775
"phenylacetaldehyde can be made by decarboxylating the bromohydrin gotten in 90%+ yield by treating cinnamic acid with bromine water"
Could anyone help me with this? Thanks!
ammonium isocyanate - 18-7-2009 at 05:52
This thread is about the oxidation of phenylacetaldehyde, not it's production. Questions about its production belong in a seperate thread.
If you are looking for a reference and can't find it on google scholar, try requesting access from a moderator to the references section of the forum
(given that this is your first post, I'm not sure they will grant it).
solo - 18-7-2009 at 06:54
...this is not a place to request articles.......but ou may not have access to the Reference section hence i will post you request here......solo
Studies of halogenohydrins and related derivatives in the cinnamic acid series. Part I
John Read and Alberta Catherine Pritchard Andrews
J. Chem. Soc., Trans. 1921, 119, 1774 - 1786,
Attachment: Studies of halogenohydrins and related derivatives in the cinnamic acid series. Part I.pdf (999kB)
This file has been downloaded 1472 times
Vogelzang - 18-7-2009 at 08:09
SYNTHESIS OF PHENYLACETIC ACID BY OXIDATION OF PHENYL ACETALDEHYDE WITH MOLECULAR OXYGEN
PRITZKOW W. ; VOERCKEL V. ; WEBER H. ;
Journal für praktische Chemie, Chemiker-Zeitung ISSN 0941-1216
1993, vol. 335, no8, pp. 705-707 [3 page(s) (article)]
Publisher Wiley, Leipzig, ALLEMAGNE (1992-1998) (Revue)
Globey - 18-7-2009 at 09:00
Pretty sure that if you oxidize phenylalanine (to phenylacetaldehyde) via aq -OCL2 route, the acid gets formed just through ambient oxidation of the
aldehyde (that is, if it doesn't 1st polymerize). Wouldn't it be nice to magically add an alpha methyl to a common amino acid, and then proceed with
the hypochlorite degradation/oxidation?
Vogelzang - 18-7-2009 at 11:52
US 3919305 Process for the preparation of phenylacetic acid
Phenylacetic acid is obtained by oxidation of phenylacetaldehyde with air or
oxygen in the presence of a transition metal derivative e.g. a derivative of Co,
Mn, Cr, Cu, Fe.
http://www.pat2pdf.org
http://ep.espacenet.com/numberSearch
Mush - 26-7-2009 at 11:59
Thank you Solo!