Selective Catalytic Methylation of Phloroglucinol with Dimethyl Carbonate in the Presence of Heterogeneous Acids

Matthew Y. Lui; Marco Noè; Anthony F. Masters; Thomas Maschmeyer

doi:10.1002/ejoc.201801112

Selective Catalytic Methylation of Phloroglucinol with Dimethyl Carbonate in the Presence of Heterogeneous Acids

Matthew Y. Lui
, Marco Noè
, Anthony F. Masters
, Thomas Maschmeyer^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

2 Citations (Scopus)

Abstract

A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl carbonate as methylating agent and solvent is described. Widely available and inexpensive solid acids have been used as catalysts to promote this transformation. H-Y zeolite proved particularly selective for monomethylation, hence it has been used for the convenient preparation of methoxyresorcinol (MR), with only limited co-production of dimethoxyphenol (DMP). Conversely, the use of tungstosilicic acid on silica easily afforded DMP in excellent isolated yield.

Original language	English
Pages (from-to)	6249-6255
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	45
DOIs	https://doi.org/10.1002/ejoc.201801112
Publication status	Published - 6 Dec 2018

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SDG 3 Good Health and Well-being
SDG 11 Sustainable Cities and Communities

User-Defined Keywords

Alkylation
Biomass
Dimethyl carbonate
Green chemistry
Heterogeneous catalysis
Solid acids

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10.1002/ejoc.201801112

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title = "Selective Catalytic Methylation of Phloroglucinol with Dimethyl Carbonate in the Presence of Heterogeneous Acids",

abstract = "A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl carbonate as methylating agent and solvent is described. Widely available and inexpensive solid acids have been used as catalysts to promote this transformation. H-Y zeolite proved particularly selective for monomethylation, hence it has been used for the convenient preparation of methoxyresorcinol (MR), with only limited co-production of dimethoxyphenol (DMP). Conversely, the use of tungstosilicic acid on silica easily afforded DMP in excellent isolated yield.",

keywords = "Alkylation, Biomass, Dimethyl carbonate, Green chemistry, Heterogeneous catalysis, Solid acids",

author = "Lui, \{Matthew Y.\} and Marco No{\`e} and Masters, \{Anthony F.\} and Thomas Maschmeyer",

note = "Funding Information: The authors thank the Australian Research Council Science and Industry Endowment Fund (SIEF, RP03-028) (M. Y. L.) and the Australia Awards Endeavour Scholarships and Fellowships (M. N.) for financial support. Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = dec,

day = "6",

doi = "10.1002/ejoc.201801112",

language = "English",

volume = "2018",

pages = "6249--6255",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Selective Catalytic Methylation of Phloroglucinol with Dimethyl Carbonate in the Presence of Heterogeneous Acids

AU - Lui, Matthew Y.

AU - Noè, Marco

AU - Masters, Anthony F.

AU - Maschmeyer, Thomas

N1 - Funding Information: The authors thank the Australian Research Council Science and Industry Endowment Fund (SIEF, RP03-028) (M. Y. L.) and the Australia Awards Endeavour Scholarships and Fellowships (M. N.) for financial support. Publisher Copyright: © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/12/6

Y1 - 2018/12/6

N2 - A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl carbonate as methylating agent and solvent is described. Widely available and inexpensive solid acids have been used as catalysts to promote this transformation. H-Y zeolite proved particularly selective for monomethylation, hence it has been used for the convenient preparation of methoxyresorcinol (MR), with only limited co-production of dimethoxyphenol (DMP). Conversely, the use of tungstosilicic acid on silica easily afforded DMP in excellent isolated yield.

AB - A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl carbonate as methylating agent and solvent is described. Widely available and inexpensive solid acids have been used as catalysts to promote this transformation. H-Y zeolite proved particularly selective for monomethylation, hence it has been used for the convenient preparation of methoxyresorcinol (MR), with only limited co-production of dimethoxyphenol (DMP). Conversely, the use of tungstosilicic acid on silica easily afforded DMP in excellent isolated yield.

KW - Alkylation

KW - Biomass

KW - Dimethyl carbonate

KW - Green chemistry

KW - Heterogeneous catalysis

KW - Solid acids

UR - https://www.scopus.com/pages/publications/85057520404

U2 - 10.1002/ejoc.201801112

DO - 10.1002/ejoc.201801112

M3 - Journal article

AN - SCOPUS:85057520404

SN - 1434-193X

VL - 2018

SP - 6249

EP - 6255

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 45

ER -

Selective Catalytic Methylation of Phloroglucinol with Dimethyl Carbonate in the Presence of Heterogeneous Acids

Abstract

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