Editing Methoxy group (section)

==Occurrence==
The simplest of methoxy compounds are [[methanol]] and [[dimethyl ether]]. Other methoxy ethers include [[anisole]] and [[vanillin]]. Many metal alkoxides contain methoxy groups, such as [[tetramethyl orthosilicate]] and [[titanium methoxide]]. [[Ester]]s with a methoxy group can be referred to as methyl esters, and the —COOCH<sub>3</sub> substituent is called a methoxycarbonyl.<ref>{{cite book |title=Introduction to organic chemistry. |last=Streitwieser |first=Andrew |date=1992 |publisher=Macmillan |others=Heathcock, Clayton H., Kosower, Edward M. |isbn=0024181706 |edition=4th |location=New York |pages=[https://archive.org/details/introductiontoor00stre_0/page/515 515] |oclc=24501305 |url-access=registration |url=https://archive.org/details/introductiontoor00stre_0/page/515}}</ref>

===Biosynthesis===
In nature, methoxy groups are found on nucleosides subjected to [[2'-O-methylation|2′-''O''-methylation]], for example, in variations of the [[five-prime cap|5′-cap structure]] known as cap-1 and cap-2. They are also common substituents in [[O-methylated flavonoid|''O''-methylated flavonoids]], whose formation is catalyzed by [[O-methyltransferase]]s that act on [[phenol]]s, such as [[catechol-O-methyl transferase|catechol-''O''-methyl transferase]] (COMT). Many natural products in plants, such as [[lignin]]s, are generated via catalysis by [[caffeoyl-CoA O-methyltransferase|caffeoyl-CoA ''O''-methyltransferase]].<ref>{{cite journal |last1=Boerjan |first1=Wout |last2=Ralph |first2=John |last3=Baucher |first3=Marie |year=2003 |title=Lignin Biosynthesis |journal=Annu. Rev. Plant Biol. |volume=54 |issue=1 | pages=519–46 |doi=10.1146/annurev.arplant.54.031902.134938 |pmid=14503002}}</ref>

===Methoxylation===
Organic methoxides are often produced by [[methylation]] of alkoxides.<ref>{{cite journal |last1=Scarrow |first1=J. A. |last2=Allen |first2=C. F. H. |year=1933 |title=Methoxyacetonitrile |journal=Org. Synth. |volume=13 |page=56 |doi=10.15227/orgsyn.013.0056}}</ref><ref>{{cite journal |last1=Cornella |first1=Josep |last2=Zarate |first2=Cayetana |last3=Martin |first3=Ruben |year=2014 |title=Ni-catalyzed Reductive Cleavage of Methyl 3-Methoxy-2-Naphthoate |journal=Org. Synth. |volume=91 |pages=260–272 |doi=10.15227/orgsyn.091.0260 |doi-access=free}}</ref> Some aryl methoxides can be synthesized by metal-catalyzed methylation of [[phenol]]s, or by methoxylation of [[aryl halide]]s.<ref>{{cite journal |last1=Cheung |first1=Chi Wai |last2=Buchwald |first2=Stephen L. |title=Mild and General Palladium-Catalyzed Synthesis of Methyl Aryl Ethers Enabled by the Use of a Palladacycle Precatalyst |journal=Organic Letters |date=2 August 2013 |volume=15 |issue=15 |pages=3998–4001 |doi=10.1021/ol401796v |pmid=23883393 |pmc=3776604}}</ref><ref>{{cite journal |last1=Tolnai |first1=Gergely L. |last2=Pethő |first2=Bálint |last3=Králl |first3=Péter |last4=Novák |first4=Zoltán |title=Palladium-Catalyzed Methoxylation of Aromatic Chlorides with Borate Salts |journal=Advanced Synthesis & Catalysis |date=13 January 2014 |volume=356 |issue=1 |pages=125–129 |doi=10.1002/adsc.201300687}}</ref>