An efficient synthesis of indole-2-acetic acid methyl esters: methyl 5-methoxyindole-2-acetate (1H-indole-2-acetic acid, 5-methoxy-, methyl ester) was written by Modi, Sandeep P.;Oglesby, R. Christopher;Archer, Sydney. And the article was included in Organic Syntheses in 1995.Synthetic Route of C8H9NO3 This article mentions the following:
A general synthetic method for the preparation in 3 steps of indole-2-acetic acid Me esters from o-nitrophenylacetic acids is described. The overall yields are 30-40% and the reactions can be carried out on a large scale. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Synthetic Route of C8H9NO3).
3-Methyl-4-nitroanisole (cas: 5367-32-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Synthetic Route of C8H9NO3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem