2-(4-Ethoxyphenyl)-2-methylpropanol
Founded in 2017, Sigma Chemical Co., Ltd. supplies over 100 countries with high-quality chemicals. We are dedicated to safety, innovation, and global cooperation.
Product Description
2-(4-Ethoxyphenyl)-2-methylpropanol is a chiral organic compound that combines an aromatic ring with a branched tertiary alcohol functional group. It features a propanol chain with a methyl group and a 4-ethoxyphenyl group attached to the 2-position, creating a tertiary carbon center. It can be synthesized through various methods, including traditional routes involving Friedel-Crafts acylation and an improved method using ionic liquids for higher yield and purity. It is primarily used as a pharmaceutical intermediate and in the synthesis of fine chemicals, offering versatility for further derivatization due to its alcohol functional group. Its applications span across the pharmaceutical, fragrance, and polymer modification industries, while handling requires standard precautions for aromatic alcohol derivatives.
Synthesis Methods
-
Route A: Aldehyde homologation + Grignard/organometal addition.
-
Steps:
-
Start from 4-ethoxybenzaldehyde (Ar-CHO).
-
Convert Ar-CHO to Ar-CO-C(CH₃)₂ (tertiary ketone).
-
Reduce the ketone to the aldehyde (Ar-C(CH₃)₂-CHO).
-
Reduce the aldehyde to the primary alcohol (Ar-C(CH₃)₂-CH₂OH) using NaBH₄.
-
-
-
Route B: Grignard addition to an α,α-dialkylated carbonyl.
-
Steps:
-
Start from 4-ethoxyacetophenone (Ar-CO-CH₃).
-
α-Alkylate to install an extra methyl (Ar-CO-C(CH₃)₂).
-
Convert the carbonyl to the aldehyde (Ar-C(CH₃)₂-CHO).
-
Reduce the aldehyde to the primary alcohol (Ar-C(CH₃)₂-CH₂OH) using NaBH₄.
-
-
-
Route C: Cross-coupling/nucleophilic substitution on a neopentyl scaffold.
-
Steps:
-
Prepare 2-methyl-2-(4-ethoxyphenyl)propanal or the corresponding bromide/chloride derivative.
-
Convert the halide to the primary alcohol (Ar-C(CH₃)₂-CH₂OH) using hydroboration/oxidation.
-
-
Uses
-
Pharmaceutical Intermediates: Useful for synthesizing bioactive molecules.
-
Fragrance and Flavor Industry: Potential use in perfumery due to its aromatic nature.
-
Material Science: Can act as a monofunctional reactive diluent or chain-end modifier for polymer synthesis.
-
Ligand or Catalyst Precursor: Useful in designing sterically hindered ligands.
-
Synthetic Intermediate: Can be converted to esters, ethers, carbamates, or oxidized to aldehydes or carboxylic acids.
Structural Information
-
IUPAC Name: 2-(4-ethoxyphenyl)-2-methylpropan-1-ol
-
Common Synonym: 2-(4-ethoxyphenyl)-2-methylpropanol
-
Molecular Formula: C₁₂H₁₈O₂
-
Molar Mass: 194.27 g/mol
-
CAS Number: 83493-63-4
-
Key Structural Features:
-
Aromatic Ring: Benzene ring substituted at the 1 and 4 (para) positions.
-
Ether Group: Para-ethoxy group (-OC₂H₅) attached to the ring.
-
Branched Carbon Chain: Tertiary carbon (2-methylpropanol part) attached directly to the ring.
-
Primary Alcohol: -OH group on a primary carbon (-CH₂OH).
-
Chirality: The molecule is achiral due to the presence of two identical methyl groups.
-
Physical Properties
-
Physical State: Solid (powder to crystal) at room temperature.
-
Melting Point: 46.0–50.0 °C.
-
Boiling Point: Predicted to be around 294.6±23.0 °C.
-
Density: Predicted to be around 1.000±0.06 g/cm³.
-
Solubility:
-
Dichloromethane: 0.576 g/L at 20 °C.
-
Hexane: 0.001 g/L at 20 °C.
-
-
pKa: Predicted to be around 15.01±0.10.
Safety and Handling
-
GHS Hazard Statements:
-
H315: Causes skin irritation.
-
H319: Causes serious eye irritation.
-
H302: Harmful if swallowed.
-
H335: May cause respiratory irritation.
-
-
Precautionary Measures:
-
P280: Wear protective gloves/eye protection/face protection.
-
P302 + P352: If on skin, wash with plenty of water.
-
P305 + P351 + P338: If in eyes, rinse cautiously with water for several minutes.
-
P271: Use outdoors or in a well-ventilated area.
-
-
Storage: Store in a cool, dark place (<15°C) to prevent degradation.