2'-Ethoxyacetophenone CAS 2142-67-8 is a specialized aromatic ketone characterized by an ethoxy substituent at the orthoposition relative to the acetyl group. This structural feature imparts distinct chemical and physical properties, making it a privileged building block for synthesizing complex molecules, particularly in the flavor/fragrance and pharmaceutical sectors.
Nombre :
2'-EthoxyacetophenoneN.º CAS :
2142-67-8MF :
C₁₀H₁₂O₂MW :
164.20Pureza :
98%Apariencia :
Typically a colorless to pale yellow liquid.Condición de almacenamiento :
Store in a tightly sealed container under an inert atmosphere (nitrogen) in a cool, dry, well-ventilated area away from heat and ignition sources.Chemical Properties
IUPAC Name: 1-(2-Ethoxyphenyl)ethan-1-one
Common Synonyms: o-Ethoxyacetophenone; 2-Acetylphenetole; 1-(2-Ethoxyphenyl)ethanone
Molecular Formula: C₁₀H₁₂O₂
Molecular Weight: 164.20 g/mol
CAS Registry Number: 2142-67-8
Chemical Structure: It consists of an acetophenone core with an ethoxy group (-OCH₂CH₃) attached at the orthoposition (carbon 2) of the benzene ring. This orthosubstitution creates steric interaction with the adjacent acetyl group.
Appearance: Typically a colorless to pale yellow liquid.
Boiling Point: ~245-248 °C (at atmospheric pressure)
Density: ~1.05-1.07 g/cm³
Refractive Index: n²⁰/D ~1.520 - 1.525
Solubility: Soluble in most organic solvents (e.g., ethanol, ether, chloroform, acetone). Practically insoluble in water.
Key Reactivity:
Ketone Carbonyl: Participates in typical carbonyl reactions: can undergo condensation (e.g., with aldehydes), reduction to the secondary alcohol, or serve as a substrate for nucleophilic addition.
Aromatic Ring: The combined electronic effects of the electron-donating ethoxy group (strong ortho/paradirector) and the electron-withdrawing acetyl group (a metadirector) result in complex directing effects for electrophilic aromatic substitution, with the ortho/parainfluence often dominating but modified by steric hindrance from the ortho-ethoxy group.
Ethoxy Group: Can be cleaved under acidic or reducing conditions (e.g., with BBr₃ or HI) to yield 2'-hydroxyacetophenone.
Biological Activities
The compound itself is primarily valued as a synthetic intermediate. Direct, significant biological activity is not its hallmark, but it finds relevance in related fields:
Fragrance & Flavor: It possesses aromatic, sweet, and slightly floral notes, making it a useful component in synthetic fragrance compositions for soaps, detergents, and cosmetic products.
Precursor to Bioactive Molecules: Serves as a key building block for synthesizing various heterocyclic compounds and chalcone derivatives, which are often screened for pharmacological activities such as antimicrobial, anti-inflammatory, or antioxidant properties.
Metabolic Studies: May be used as a substrate or model compound in studies examining the metabolism of alkyl aryl ketones.
Biosynthesis
2'-Ethoxyacetophenone is not known to be produced via natural biosynthesis for commercial purposes. It is synthesized industrially and in the laboratory through chemical methods:
1.Friedel-Crafts Acylation: The most common route involves the aluminum chloride (AlCl₃) catalyzed acylation of phenetole (ethoxybenzene) with acetyl chloride or acetic anhydride. Regioselectivity favors the orthoand paraproducts, with the orthoisomer often separable due to its distinct physical properties.
2.Etherification of 2'-Hydroxyacetophenone: An alternative method involves the Williamson ether synthesis, alkylating 2'-hydroxyacetophenone with ethyl halide (e.g., iodoethane) in the presence of a base.
Applications
Key Advantages & Benefits
1. Strategic Steric Hindrance for Controlled Reactivity
Benefit: The ortho-positioned ethoxy group creates pronounced steric hindrance around the carbonyl carbon. This slows down certain reactions, allowing for better selectivity and control in transformations compared to less-hindered isomers. It can suppress unwanted side reactions and promote cleaner product formation.
Application Scenario: In the synthesis of a specific benzofuran via an intramolecular aldol condensation, using 2'-Ethoxyacetophenone as a precursor ensures the reaction proceeds in a controlled manner. The steric bulk helps dictate the approach of the nucleophile, favoring the desired cyclization pathway and minimizing polymerization or by-product formation, leading to higher yields of the heterocyclic core.
2. Dual Functional Group with Orthogonal Stability
Benefit: The molecule features two robust functional groups: the ketone (for C-C bond formation) and the ether (for stability and later cleavage). The ethoxy group is stable under a wide range of basic and nucleophilic conditions used for ketone chemistry, but can be selectively cleaved later under acidic conditions (e.g., with BBr₃) to reveal a phenolic -OH, enabling a powerful two-stage synthetic strategy.
Application Scenario: A medicinal chemist can first utilize the ketone in a high-throughput Suzuki coupling to create a library of biaryl compounds with the ethoxy group intact, ensuring solubility and directing effects. In a subsequent step for a promising lead candidate, the ethoxy group can be selectively dealkylated to a phenol, enabling further derivatization (e.g., sulfation, glycosylation) to fine-tune pharmacokinetic properties.
3. A Distinct Flavor/Fragrance Profile
Benefit: The ortho-ethoxy substitution imparts a characteristic sweet, floral, and slightly honey-like aroma that is distinct from its metaand paraisomers. This makes it a valuable and sometimes irreplaceable ingredient for creating nuanced, sophisticated accords in perfumery.
Application Scenario: A perfumer crafting a complex floral fantasy fragrance seeking a honeyed, rosy nuance will specifically select 2'-Ethoxyacetophenone over other isomers. Its unique scent profile provides a specific olfactory effect that contributes to the fragrance's unique character and complexity, where a simple acetophenone would be too generic.
2'-Ethoxyacetophenone is the specialist's isomer within the ethoxyacetophenone family. Its value proposition is not based on high reactivity or low cost, but on strategic steric and functional group control. It is the preferred choice when a synthesis demands the modulated reactivity of a ketone adjacent to a protecting/directing group, or when a specific, rich honey-floral note is required in a fragrance formulation. For applications where molecular crowding or a specific olfactory signature is critical, it offers advantages that simpler, more linear analogs cannot match.
FAQs
Q1: How does the ortho-ethoxy group in this compound affect its reactivity compared to the paraisomer?
A1: The ortho-ethoxy group introduces significant steric hindrance adjacent to the reactive carbonyl. This can slow down certain nucleophilic additions or condensations at the ketone compared to the paraisomer. Furthermore, in electrophilic aromatic substitution, it directs incoming groups primarily to the paraposition (C5) but the steric bulk can also influence regioisomer ratios and reaction rates.
Q2: What are the critical storage conditions to maintain product quality?
A2: Store in a tightly sealed container under an inert atmosphere (nitrogen) in a cool, dry, well-ventilated area away from heat and ignition sources. It is recommended to store at 2-8°C for long-term stability to prevent oxidation and discoloration. Keep away from strong oxidizing agents and bases.
Q3: Is selective reduction of the ketone to the alcohol feasible without cleaving the ethoxy group?
A3: Yes. The ethoxy ether bond is stable to common reducing agents for ketones. Sodium borohydride (NaBH₄) in methanol is an excellent choice for the clean and selective reduction of the acetyl group to produce 1-(2-ethoxyphenyl)ethanol. More powerful agents like LiAlH₄ will also reduce the ketone but require strictly anhydrous conditions.
Q4: Can this compound be used in Friedel-Crafts alkylation or other EAS reactions on the ring?
A4: It is possible but challenging and requires careful optimization. The ring is deactivated by the acetyl group, and the ortho-ethoxy group creates steric congestion. Reactions like nitration or halogenation will occur but may be slower than with unsubstituted acetophenone and yield mixtures where the paraposition (relative to the ethoxy) is favored. Isomer separation may be necessary.
Q5: What are typical purity specifications, and how is it analyzed?
A5: Commercial material is typically offered at ≥97% purity (by GC). Quality control is primarily performed using Gas Chromatography (GC) for purity and ¹H NMR for structural confirmation. The product should be a clear, colorless to faint yellow liquid.
Q6: Is this material readily available for process-scale development, or is it a specialty item?
A6: It is considered a specialty fine chemical. While available from several suppliers, it is not produced on the same multi-ton scale as commodity acetophenones. For kilogram-scale requests and above, lead times may be longer, and direct engagement with suppliers for specific quotes and project planning is strongly advised.
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