What is the Difference Between Anisole and Cresol

The key difference between anisole and cresol is that anisole does not react with neutral ferric chloride, whereas cresol reacts with neutral ferric chloride to give a violet color.

Anisole and cresol are organic compounds that are position isomers of each other. These two compounds have the same chemical formula because they are isomers of each other. However, both these compounds have a benzene ring attached to an oxygen atom. In anisole, this oxygen atom is attached to a methyl functional group, whereas in cresol, the oxygen atom is attached to a hydrogen atom, and there is a methyl group attached to the adjacent carbon atom of the benzene ring.

CONTENTS

1. Overview and Key Difference
2. What is Anisole
3. What is Cresol
4. Anisole vs Cresol in Tabular Form
5. Summary – Anisole vs Cresol 

What is Anisole?

Anisole is an organic compound having the chemical formula CH3OC6H5. This is an ether compound having a methyl group and a phenyl group attached to the same central oxygen atom. It occurs as a colorless liquid and has an odor that resembles the odor of anise seed. We can observe the presence of this compound in many natural and artificial fragrances. It is mainly a synthetic compound we can use for the synthesis of other organic compounds as a precursor. Anisole can be produced via methylation of sodium phenoxide in the presence of dimethyl sulfate or methyl chloride.

Anisole can undergo electrophilic aromatic substitution reactions. The methoxy group of the compound is an ortho/para directing group. This methoxy group has a high impact on the electron cloud of the ring structure attached to the oxygen atom. Moreover, anisole is able to undergo electrophilic reactions as well. For example, anisole reacts with acetic anhydride, forming 4-methoxyacetophenone. The ether linkage of this compound is very stable, but the methyl group is easily replaced by hydrochloric acid. Anisole is generally categorized as a non-toxic compound, but it is a flammable liquid.

What is Cresol?

Cresol is an organic compound having the chemical formula HO-C6H4-CH3. Since it contains a phenol substituted with a methyl group, we can call it “methylphenol” as well. Moreover, this compound can be either natural or synthetic. Depending on the substitution of the methyl group, there are three structural isomers of cresol as ortho-, para- and meta-substituted cresol. These three forms can occur in the same mixture; we call it “tricresol.” Mostly, cresol is obtained from coal tar. The synthetic forms are produced via methylation of phenol. In addition, hydrolysis of chlorotoluene can form cresol.

Moreover, cresol can exist in solid, liquid, or gas phases because their melting and boiling points are not far from room temperature. Upon long exposure to air, this compound can slowly undergo oxidation. Usually, cresol is a colorless compound, but the presence of impurities can cause yellow or brown coloration. Furthermore, cresol has an odor resembling the typical phenol odor.

Besides, there are many important applications of cresol. For example, it is useful as a precursor for materials such as plastics, pesticides, pharmaceuticals, and dyes. However, inhalation or ingestion of cresol can cause harmful effects on us. Some toxic effects include irritation of the skin, eyes, mouth, and throat. In addition, it can cause abdominal pain and vomiting.

What is the Difference Between Anisole and Cresol?

Anisole is an organic compound having the chemical formula CH3OC6H5, while cresol is an organic compound having the chemical formula HO-C6H4-CH3. The key difference between anisole and cresol is that anisole does not react with neutral ferric chloride, whereas cresol reacts with neutral ferric chloride to give a violet color.

The below infographic presents the differences between anisole and cresol in tabular form for side by side comparison.

Summary – Anisole vs Cresol

Anisole and cresol are organic compounds that are position isomers of each other. The key difference between anisole and cresol is that anisole does not react with neutral ferric chloride, whereas cresol reacts with neutral ferric chloride to give a violet color.

Reference:

1. “Anisole.” National Center for Biotechnology Information. PubChem Compound Database, U.S. National Library of Medicine.

Image Courtesy:

1. “Anisole” By MDaxo – Own work (CC BY-SA 4.0) via Commons Wikimedia
2. “Cresol isomers” By H Padleckas (CC BY-SA 3.0) via Commons Wikimedia