Courses
Courses for Kids
Free study material
Offline Centres
More
Store Icon
Store

How is anisole converted into 2-Methoxy toluene?

seo-qna
SearchIcon
Answer
VerifiedVerified
455.4k+ views
Hint: Anisoles have a methoxy group on the benzene ring, it is an ortho substituting group. When methyl group attacks at the anisole group, it gets attached to the ortho position. $AlC{{l}_{3}}$ act as a lewis acid.

Complete step by step answer:
Anisole or methoxybenzene, is an organic compound with the formula $C{{H}_{3}}O{{C}_{6}}{{H}_{5}}$. It is a colourless liquid with a smell reminiscent of anise seed, and in many of its derivatives are found in natural and artificial fragrances. The structure of anisole is as follows:
seo images

The structure of 2-methoxytoluene is given as follows:
seo images

The following synthesis can be done using Friedel Craft alkylation. The friedel-crafts reaction are a set of reactions developed by Charles Friedel and James Craft in 1877 to attach substituents to an aromatic ring. Friedel-Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic substitution.
Friedel Craft reaction proceeds through use of a lewis acid. In the question given above, we have anisole as a substrate and $AlC{{l}_{3}}$ is used as a lewis acid.Methyl chloride is the attacking species. Lewis acid, $AlC{{l}_{3}}$, takes up the chloride from the methyl chloride and electrophile $C{{H}_{3}}^{+}$, methyl cation is generated. This methyl cation attacks on the anisole, at the ortho position.
The reaction of the conversion of anisole to 2-methoxytoluene is as follows:
seo images


Note: $AlC{{l}_{3}}$ is a lewis acid because it can accept electrons. Aluminium has vacant orbitals and is strong electrophile due to presence of high electron negative Chlorine atoms which reduces the electron density from the central atom.