Fast and Green Microwave-Assisted Conversion of Essential Oil Allylbenzenes into the Corresponding Aldehydes via Alkene Isomerization and Subsequent Potassium Permanganate Promoted Oxidative Alkene Group Cleavage

Thi Xuan Thi Luu, Trinh To Lam, Thach Ngoc Le, Fritz Duus

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

Essential oil allylbenzenes from have been converted quickly and efficiently into the corresponding benzaldehydes in good yields by a two-step "green" reaction pathway based on a solventless alkene group isomerization by KF/Al2O3 to form the corresponding 1-arylpropene and a subsequent solventless oxidation of the latter to the corresponding benzaldehyde by KMnO4/CuSO4 center dot 5H(2)O. The assistance by microwave irradiation results in very short reaction times (<15 minutes). The green conversion of eugenol (4-allyl-2-methoxyphenol) into vanillin (4-hydroxy-3-methoxybenzaldehyde) has been carried out in a similar way, requiring however two additional microwave-assisted synthetic steps for acetylation of the hydroxy group prior to the oxidation reaction, and for the final deacetylation of vanillin acetate (4-acetoxy-3-methoxybenzaldehyde) by KF/Al2O3 under solvent-free conditions, respectively.
OriginalsprogEngelsk
TidsskriftMolecules
Vol/bind14
Udgave nummer9
Sider (fra-til)3411-3424
ISSN1420-3049
DOI
StatusUdgivet - 2009

Citer dette

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title = "Fast and Green Microwave-Assisted Conversion of Essential Oil Allylbenzenes into the Corresponding Aldehydes via Alkene Isomerization and Subsequent Potassium Permanganate Promoted Oxidative Alkene Group Cleavage",
abstract = "Essential oil allylbenzenes from have been converted quickly and efficiently into the corresponding benzaldehydes in good yields by a two-step {"}green{"} reaction pathway based on a solventless alkene group isomerization by KF/Al2O3 to form the corresponding 1-arylpropene and a subsequent solventless oxidation of the latter to the corresponding benzaldehyde by KMnO4/CuSO4 center dot 5H(2)O. The assistance by microwave irradiation results in very short reaction times (<15 minutes). The green conversion of eugenol (4-allyl-2-methoxyphenol) into vanillin (4-hydroxy-3-methoxybenzaldehyde) has been carried out in a similar way, requiring however two additional microwave-assisted synthetic steps for acetylation of the hydroxy group prior to the oxidation reaction, and for the final deacetylation of vanillin acetate (4-acetoxy-3-methoxybenzaldehyde) by KF/Al2O3 under solvent-free conditions, respectively.",
keywords = "microwave irradiation, solvent-free reaction, alkene isomerization, alkene oxidation",
author = "Luu, {Thi Xuan Thi} and Lam, {Trinh To} and Le, {Thach Ngoc} and Fritz Duus",
year = "2009",
doi = "10.3390/molecules14093411",
language = "English",
volume = "14",
pages = "3411--3424",
journal = "Molecules",
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Fast and Green Microwave-Assisted Conversion of Essential Oil Allylbenzenes into the Corresponding Aldehydes via Alkene Isomerization and Subsequent Potassium Permanganate Promoted Oxidative Alkene Group Cleavage. / Luu, Thi Xuan Thi; Lam, Trinh To; Le, Thach Ngoc; Duus, Fritz.

I: Molecules, Bind 14, Nr. 9, 2009, s. 3411-3424.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Fast and Green Microwave-Assisted Conversion of Essential Oil Allylbenzenes into the Corresponding Aldehydes via Alkene Isomerization and Subsequent Potassium Permanganate Promoted Oxidative Alkene Group Cleavage

AU - Luu, Thi Xuan Thi

AU - Lam, Trinh To

AU - Le, Thach Ngoc

AU - Duus, Fritz

PY - 2009

Y1 - 2009

N2 - Essential oil allylbenzenes from have been converted quickly and efficiently into the corresponding benzaldehydes in good yields by a two-step "green" reaction pathway based on a solventless alkene group isomerization by KF/Al2O3 to form the corresponding 1-arylpropene and a subsequent solventless oxidation of the latter to the corresponding benzaldehyde by KMnO4/CuSO4 center dot 5H(2)O. The assistance by microwave irradiation results in very short reaction times (<15 minutes). The green conversion of eugenol (4-allyl-2-methoxyphenol) into vanillin (4-hydroxy-3-methoxybenzaldehyde) has been carried out in a similar way, requiring however two additional microwave-assisted synthetic steps for acetylation of the hydroxy group prior to the oxidation reaction, and for the final deacetylation of vanillin acetate (4-acetoxy-3-methoxybenzaldehyde) by KF/Al2O3 under solvent-free conditions, respectively.

AB - Essential oil allylbenzenes from have been converted quickly and efficiently into the corresponding benzaldehydes in good yields by a two-step "green" reaction pathway based on a solventless alkene group isomerization by KF/Al2O3 to form the corresponding 1-arylpropene and a subsequent solventless oxidation of the latter to the corresponding benzaldehyde by KMnO4/CuSO4 center dot 5H(2)O. The assistance by microwave irradiation results in very short reaction times (<15 minutes). The green conversion of eugenol (4-allyl-2-methoxyphenol) into vanillin (4-hydroxy-3-methoxybenzaldehyde) has been carried out in a similar way, requiring however two additional microwave-assisted synthetic steps for acetylation of the hydroxy group prior to the oxidation reaction, and for the final deacetylation of vanillin acetate (4-acetoxy-3-methoxybenzaldehyde) by KF/Al2O3 under solvent-free conditions, respectively.

KW - microwave irradiation

KW - solvent-free reaction

KW - alkene isomerization

KW - alkene oxidation

U2 - 10.3390/molecules14093411

DO - 10.3390/molecules14093411

M3 - Journal article

VL - 14

SP - 3411

EP - 3424

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 9

ER -