Methoxy group

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. Esters with a methoxy group can be referred to as methyl esters, and the —COOCH3 substituent is called a methoxycarbonyl.

Biosynthesis

In nature, methoxy groups are found on nucleosides subjected to 2′-O-methylation, for example, in variations of the 5′-cap structure known as cap-1 and cap-2. They are also common substituents in O-methylated flavonoids, whose formation is catalyzed by O-methyltransferases that act on phenols, such as catechol-O-methyl transferase (COMT). Many natural products in plants, such as lignins, are generated via catalysis by caffeoyl-CoA O-methyltransferase.

Methoxylation

Organic methoxides are often produced by methylation of alkoxides. Some aryl methoxides can be synthesized by metal-catalyzed methylation of phenols, or by methoxylation of aryl halides.

References

References

1. Streitwieser, Andrew. (1992). "Introduction to organic chemistry.". Macmillan.
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4. (2014). "Ni-catalyzed Reductive Cleavage of Methyl 3-Methoxy-2-Naphthoate". Org. Synth..
5. (2 August 2013). "Mild and General Palladium-Catalyzed Synthesis of Methyl Aryl Ethers Enabled by the Use of a Palladacycle Precatalyst". Organic Letters.
6. (13 January 2014). "Palladium-Catalyzed Methoxylation of Aromatic Chlorides with Borate Salts". Advanced Synthesis & Catalysis.