Configuration of Diastereoisomeric 3-Methoxy-4-Hydroxyphenylpropanolamines

Fodor, Gyula; Kiss, Joseph E.; Szekerke, M.

doi:10.1021/jo01148a001

Cited by 14 publications

(2 citation statements)

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“…These reagents are usually prepared from carboxylic acids, and therefore, it would be desirable if the acylations could be carried out by using carboxylic acids directly as acylating agents. [9][10][11] In this paper we describe the direct C-acylation of phenol and naphthol derivatives catalyzed by graphite in methanesulfonic acid (GMA) using carboxylic acids as acylating reagents.…”

mentioning

confidence: 99%

Direct Acylation of Phenol and Naphthol Derivatives in a Mixture of Graphite and Methanesulfonic Acid

Sharghi¹,

Hosseini‐Sarvari²,

Eskandari³

2006

Synthesis

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confidence: 99%

Direct Acylation of Phenol and Naphthol Derivatives in a Mixture of Graphite and Methanesulfonic Acid

Sharghi¹,

Hosseini‐Sarvari²,

Eskandari³

2006

Synthesis

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“…(21) to the a-oximino lietone, which was hydrolyzed to the diketone with 2% HC1 a t reflux or with 12 i V H?SO., a t room tenlperature. The yello\v diketone was extracted with benzene and recrystallized from petroleu111 ether, m.p.…”

Section: Etha~lolysis Of L -H Y D R O X V -L -( 4 -L~y D R O S Y -3 -mentioning

confidence: 99%

Lignin Model Compounds: Ii. Preparation and Properties of 1-Hydroxy-1-(4-Hydroxy-3-Methoxyphenyl)-2-Propanone

Gardner¹,

Henderson²,

MacLean³

1962

Can. J. Chem.

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Modern concepts of lignin structure suggest that the ketol 1-hydroxy-1-(4-hydroxy-3-methoxypheny1)-2-propanone, VI, should be detectable in the hydrolysis products of lignin and wood. A reference sample of VI, previously unavailable, has now been prepared by catalytic hydroge~lation of the dilretone 1-(Phydrosy-3-methoxyphenyl)-1,2-proparedione 11. Both fermentative and catalytic hydrogenation of I 1 gave mixtures of, according to paper chromatography, mainly 2-hydroxy-l-(4-hydroxy-3-methoxyphenyl)-l-propa101e, V ; the desired ketol, VI; small amounts of vanillic acid; and traces of guaiacyl acetone and an unknown phenolic compound. The ketol VI was isolated from the catalytic hydrogenation products by solvent fractionation and was identified by absorption spectra, derivatives, and comparison with the other two possible isomeric ketols. Dilute alkali converted VI to the isomeric ketol V. Both ethanolysis and acidolysis of VI gave the same monomeric products as lignin.Since the discovery by Hibbert and co-workers (1) that the four guaiacplpropane derivatives I-IV were produced by refluxing extractive-free coniferous wood with ethanol containing a small percentage of hydrogen chloride, extensive studies have been conducted on related monomers and dimers as model compounds for lignin reactions. In this way significant new laowledge of lignin structure and behavior has been acquired.In seeking an explarlation for the formation from lignin of the "ethanolysis" products, the synthesis and study of the three isomeric a-ketols V, VI, and VII were undertaken by the Hibbert group. T h e synthesis of V, 2-hydroxy-1-(4-hydroxy-3-methoxypheny1)-1-propanone, and VII, 3-hydroxy -1-(4-hydroxy -3-methoxyphenyl) -2-propanone, was accolnplished (2, 3) but repeated attempts failed to provide VI, 1-hydroxy-1-(4-hydroxy-3-methoxyphen~71)-2-propmone, and therefore it was necessary to perform ethanolysis and other reactions on its diacetate (4). Wacek and I-Iorak (5) also attempted to prepare VI but found, as had Mitchell (6), that even very mild deacetylation techniclues applied to the diacetate of VI invariably resulted in rearrangement to the more stable V. These filldings were in accord with the results obtained with related alkylaryl a-ketols by Auwers and No11 (7) and Temnikova (8). Thus methylbenzoyl carbinol (V, R = phenyl) rearranged with a variety of reagents to phenylacetyl carbinol (VI, R = phenyl) whereas

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Boron Trifluoride

Heaney

2001

Encyclopedia of Reagents for Organic Synthesis

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Configuration of Diastereoisomeric 3-Methoxy-4-Hydroxyphenylpropanolamines

Cited by 14 publications

References 7 publications

Direct Acylation of Phenol and Naphthol Derivatives in a Mixture of Graphite and Methanesulfonic Acid

Direct Acylation of Phenol and Naphthol Derivatives in a Mixture of Graphite and Methanesulfonic Acid

Lignin Model Compounds: Ii. Preparation and Properties of 1-Hydroxy-1-(4-Hydroxy-3-Methoxyphenyl)-2-Propanone

Boron Trifluoride

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