3-Methoxybenzyl alcohol
[CAS# 6971-51-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic alcohol
• Name: 3-Methoxybenzyl alcohol
• Synonyms: 3-Anise alcohol; m-Anisyl alcohol
• Molecular Formula: C₈H₁₀O₂
• Molecular Weight: 138.16
• CAS Registry Number: 6971-51-3
• EC Number: 230-200-5
• SMILES: COC1=CC=CC(=C1)CO

Properties

• Density: 1.112
• Boiling point: 250 °C (723 mmHg)
• Refractive index: 1.5425-1.5445
• Water solubility: immiscible

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

3-Methoxybenzyl alcohol, also known as m-anisyl alcohol, is an organic compound with the molecular formula C₈H₁₀O₂. It belongs to the class of benzyl alcohol derivatives, characterized by the presence of a methoxy group at the meta-position on the aromatic ring. This compound is a colorless to pale yellow liquid that exhibits a mild aromatic odor and demonstrates solubility in organic solvents such as ethanol and ether. It has attracted interest due to its relevance in synthetic organic chemistry and its role as an intermediate in the production of various chemical products.

The discovery of 3-methoxybenzyl alcohol can be linked to the broader investigations into substituted benzyl alcohols, a group of compounds that became subjects of study during the early developments of synthetic organic chemistry in the late 19th and early 20th centuries. The identification and characterization of such compounds were facilitated by the progressive refinement of techniques such as fractional distillation, crystallization, and infrared spectroscopy. The methoxylation of benzyl alcohol derivatives emerged as a synthetic route that was readily accessible, enabling the selective formation of positional isomers such as ortho-, meta-, and para-methoxybenzyl alcohols.

In laboratory synthesis, 3-methoxybenzyl alcohol is commonly prepared via reduction of the corresponding aldehyde, 3-methoxybenzaldehyde. This reaction can be accomplished using classical reducing agents like sodium borohydride or lithium aluminum hydride. Alternatively, catalytic hydrogenation techniques can be employed, where hydrogen gas is used in the presence of a transition metal catalyst such as palladium on carbon. These methods offer reliable yields and are suitable for producing the compound on a preparative scale.

One of the primary applications of 3-methoxybenzyl alcohol is its use as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It serves as a building block in the preparation of more complex aromatic compounds that contain methoxy or hydroxyl functionalities. Its structural features make it a useful precursor in the formation of ethers, esters, and amines via standard substitution or condensation reactions. For instance, the hydroxyl group of the alcohol can be activated and then displaced by various nucleophiles, while the methoxy group can influence the reactivity of the aromatic ring through electron-donating resonance effects.

In medicinal chemistry, 3-methoxybenzyl alcohol derivatives have been investigated for their biological activity and potential therapeutic effects. The methoxybenzyl moiety appears in several bioactive compounds, and structural analogs have been synthesized to evaluate their influence on pharmacological profiles. Though 3-methoxybenzyl alcohol itself is not a marketed drug, its utility in medicinal chemistry lies in its role as a versatile synthetic intermediate for exploring structure-activity relationships.

Another area where 3-methoxybenzyl alcohol finds relevance is in the synthesis of fragrances and flavoring agents. Methoxy-substituted aromatic alcohols are known to contribute sweet, balsamic, and floral notes to perfumery compositions. The compound may be used either directly or as a precursor to esters and acetals with enhanced olfactory properties. In the flavor and fragrance industry, its chemical structure is favorable for modifying the aromatic character of blends, and it participates in reactions that generate complex aromatic molecules with improved sensory attributes.

Furthermore, 3-methoxybenzyl alcohol has been utilized in material science and polymer chemistry as a monomeric unit or modifying agent. It can be incorporated into polymers to impart specific characteristics such as increased hydrophilicity or to influence thermal properties. Additionally, it is used in academic research as a reference compound for studying the influence of substituents on the reactivity and physicochemical properties of aromatic alcohols.

All these applications reflect the compound’s value in both industrial and research settings. Its availability and chemical reactivity make it an important tool for chemists aiming to design and develop functional materials or bioactive compounds. Continued interest in substituted benzyl alcohols ensures that 3-methoxybenzyl alcohol will remain a compound of practical significance in the toolbox of synthetic organic chemistry.

References

2006. Sodium borohydride reduction of aromatic carboxylic acids via methyl esters. Journal of Chemical Sciences, 118(5).
DOI: 10.1007/bf02711452

2018. Sulfuric Acid-Promoted Oxidation of Benzylic Alcohols to Aromatic Aldehydes in Dimethyl Sulfoxide: An Efficient Metal-Free Oxidation Approach. Synlett, 29(11).
DOI: 10.1055/s-0037-1609149

2022. Catalytic Hydrothermal Liquefaction of Algae for Production of Bio-oil with Solid Superacid Catalyst SO42−/ZrO2. Journal of Ocean University of China, 21(5).
DOI: 10.1007/s11802-022-5124-x