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Methyl phenylacetate - Wikipedia

ethyl phenyl acetate note:0.05 - phenethyl phenyl acetate0.01 - phenyl propyl alcohol Imitation fruit flavouring ingredient

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Synthesis description for preparation of PHENYL ACETATE

One-pot synthesis of methyl -phenyl carbamate (MPC) from aniline, urea, and methanol is a green reaction route. However, along which reaction path the reaction proceeds is still unclear and thereby the reaction mechanism cannot be determined. So the present work put much more emphasis on the analysis of the reaction path of MPC synthesis from aniline, urea, and methanol. First, the components in this reaction system were identified by means of gas-phase chromatograph (GC), high-performance liquid chromatograph (HPLC), and HPLC–mass spectrometry (MS) analyses. On the basis of the change tendency of the reaction components with reaction time, five plausible reaction paths were conjectured: one proceeds via a dimethyl carbonate intermediate, another utilizes methyl carbamate as an intermediate, still another passes a 1-phenyl biuret intermediate, yet another takes place through a phenylurea intermediate, and the last one carries on using diphenylurea as an intermediate. Then on the basis of thermodynamic analysis of the five possible reaction paths in combination with necessary experimental verifications, the one via a phenylurea intermediate was determined as the major reaction path in the absence of catalyst. Lastly, the influence of catalyst on the reaction path was studied and the result showed that the reaction path changed from through the phenylurea intermediate to the methyl carbamate intermediate in the presence of γ-Al2O3 catalyst.

Methyl phenylacetate is an organic compound that is the ester formed from methanol and ..

The route began with a fairly standard reaction - the addition of methylmagnesium bromide to an enone in the presence of catalytic copper(I) and LiCl, followed by quenching with gaseous formaldehyde. This was followed by a rather useful but little known reaction; the Takai-Oshima-Lombardo methylenation of the ketone.[1] The newly formed alcohol was then oxidised under Swern conditions and treated with propen-2-yl magnesium bromide, followed by methyl chloroformate, to give the expected allyl carbonate. Next came the route's sexy step - a cool carbonylative metal ene-reaction. Thus, heating the carbonate in wet acetic acid with palladium(II) acetate and triphenyl phosphine under a single atmosphere of CO gave the hydrindane acid in quite reasonable yield. So far so good.

methyl phenyl acetate | Sigma-Aldrich

Good luck with finishing your thesis! I’m sure selenophenol is delightful. Also, you deleted the gem-dimethyl in your second figure.

3. In retrospect, with the product and starting material shown it's not too hard to see what's going on. Presumably the double bond moves into conjugation with the sulfone, addition-elimination of bromide occurs, and then the double bond moves out of conjugation again (for some reason). Not sure I'd want to try and explain why to a room full of chemists. So, why even bother with the thiophenol? Well, the authors say that they originally just tried aqueous hydroxide in methanol - typical hydrolysis conditions - but these resulted in a similar substitution of bromide by methoxide, but with the double bond remaining in conjugation with the sulfone! Unfortunately, this messed up the next step, which required the double bond where it was, so the conditions had to be changed. How they knew that addition thiophenol would help (or why they'd try it if they didn't) is beyond me.

1. As far as I know you can only carry this out as a methylenation (i.e. to introduce a =CH2), like a Tebbe reaction. Also like the Tebbe, it seems to be very useful where other olefinations fail. A friend of mine had trouble methylenating some halogenated 3-acetyl indoles - normal Wittig, Tebbe and Peterson conditions just didn't do anything, nor did the compounds react well with methylmagnesium bromide or methyllithium. The Takai-Lombardo worked great, though!

Search results for methyl phenyl acetate at Sigma-Aldrich

Present in cocoa, coffee and strawberryMethyl phenylacetate is an organic compound that is the ester formed from methanol and phenylacetic acid.

Methyl Phenyl Acetate, also known as Methyl 2-phenyl acetate or Methyl benzene acetate, is an organic compound and the ester formed from phenylacetic acid and methanol; it is used in the perfume and flavor industry to create a similar scent to honey. Ungraded products supplied by Spectrum are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for human consumption or therapeutic use. These materials may or may not have a Certificate of Analysis available.

Methyl Phenyl Acetate, also known as Methyl 2-phenyl acetate or Methyl benzene acetate, is an organic compound and the ester formed from phenylacetic acid and methanol; it is used in the perfume and flavor industry to create a similar scent to honey. Ungraded products supplied by Spectrum are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for human consumption or therapeutic use. These materials may or may not have a Certificate of Analysis available.

methyl phenyl acetate, 101-41-7 - The Good Scents …
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  • methyl phenylacetate - Synthesis - The Pherobase

    Phenyl Acetate is an aromatic fatty acid metabolite of phenylalanine with potential antineoplastic activity

  • ethyl phenylacetate - Synthesis

    methyl phenyl acetate: ..

  • One-pot synthesis of methyl N-phenyl ..

    METHYL PHENYLACETATE FOR SYNTHESIS Find MSDS or SDS, a COA, data sheets and more information.

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N-Methyl-D-Aspartate; phenyl acetate;

The carboxylic acid was the converted to its methyl ester by alkylation with iodomethane; I guess a Fisher-type esterification here is probably not a good idea. This was followed up by a ring expansion using dibromocarbene, which formed the expected cyclopropane, followed by treatment with p-methoxythiophenol and potassium carbonate in hexafluoroisopropanol to opening up the new ring with loss of bromide.[2] Finally, the thioether was oxidised to the sulfone with two equivalents of m-CPBA. This is where things a get a bit silly, as treatment with thiophenol in aqueous hydoxide - methanol then give the acid shown... with replacement of bromide by thiophenol![3] The acid was then coupled with selenophenol, using the horrific looking phenyl dichlorophosphate as a coupling agent. Ewww. Irradiation of the selenoester in the presence of hexabutyl ditin (!) then lead to a non-reductive radical cyclisation onto the nearby double bond with loss of the sulfone by fragmentation. Low temperature desulfurisation with RaNi and hydrogenation of the remaining double bond with Adam's catalyst gave the tricyclic ketone in impressive yield. The group were now only a Wolff rearrangement and a reduction away from victory. Introduction of the diazo group required for the Wolff rearrangement was carried out in two steps, first making the oxime by treatment with isoamyl nitrite and then using ammonium hydroxide and bleach to form the α-diazoketone. Finally, photolysis in methanol carried out the expected ring contraction to give the cyclobutane methyl ester that was then converted to the required aldehyde. Nature doesn't make many cyclobutanes, but I'd say Koreeda's synthesis of this one is pretty neat.

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