55685-75-1

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-2-methoxybenzyl alcohol is used as an intermediate in the synthesis of pharmaceutical compounds for its ability to be easily modified and incorporated into complex molecular structures. Its presence in the molecular backbone can contribute to the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 4-chloro-2-methoxybenzyl alcohol is used as a building block for the development of new pesticides and herbicides. Its chemical structure allows for the creation of compounds that can effectively target and control pests and weeds, thereby enhancing crop protection.
Used in Flavor and Fragrance Industry:
4-Chloro-2-methoxybenzyl alcohol is used as a key component in the formulation of fragrances and flavorings. Its unique aromatic profile can contribute to the creation of distinct scents and tastes, making it valuable in the development of consumer products such as perfumes, colognes, and food additives.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 4-chloro-2-methoxybenzyl alcohol is utilized as a precursor for the synthesis of various dyes and pigments. Its chemical properties enable the production of colorants with specific characteristics, such as brightness, stability, and solubility, which are essential for applications in textiles, plastics, and printing inks.
Used in Research and Development:
4-Chloro-2-methoxybenzyl alcohol is also used in research and development settings as a versatile compound for exploring new chemical reactions and syntheses. Its reactivity and structural features make it an attractive candidate for studying novel chemical pathways and developing innovative materials and compounds.

InChI:InChI=1/C8H9ClO2/c1-11-8-4-7(9)3-2-6(8)5-10/h2-4,10H,5H2,1H3

Synthetic route

methanol (67-56-1) + 4-chlorobenzaldehyde (104-88-1) → 4-chlorobenzaldehyde methyl hemiacetal (55685-75-1)

Conditions	Yield
In 1,4-dioxane at 24.9℃; Equilibrium constant; Rate constant;
With hydrogenchloride; lithium acetate In 1,4-dioxane at 24.85℃; pH=4.0; Equilibrium constant; Kinetics; Further Variations:; Solvents; concentrations; Reduction; hemiacetalization; Electrochemical reaction;
With potassium tert-butylate In d(4)-methanol at 20℃; for 2h; Equilibrium constant;

methanol (67-56-1) + 2,2,2-trichloro-1-(4-chlorophenyl)ethanone (27704-37-6) → Methyl 4-chlorobenzoate (1126-46-1) + 4-chlorobenzaldehyde methyl hemiacetal (55685-75-1)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;

bromochlorobenzene (106-39-8) → Methyl 4-chlorobenzoate (1126-46-1) + 4-chlorobenzaldehyde methyl hemiacetal (55685-75-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium chloride; magnesium / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 1.2: 0.5 h / 0 °C / Inert atmosphere 1.3: 2 h / 0 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere View Scheme

4-chlorobenzaldehyde methyl hemiacetal (55685-75-1) → methanol (67-56-1) + 4-chlorobenzaldehyde (104-88-1)

Conditions	Yield
In 1,4-dioxane at 24.9℃; Equilibrium constant;

4-chlorobenzaldehyde methyl hemiacetal (55685-75-1) → 4-chlorobenzaldehyde (104-88-1)

Conditions	Yield
With hydrogenchloride; lithium acetate In 1,4-dioxane; methanol at 24.85℃; pH=4.0; Equilibrium constant; Further Variations:; concentrations; Disproportionation; Electrochemical reaction;

4-chlorobenzaldehyde methyl hemiacetal (55685-75-1) → Methyl 4-chlorobenzoate (1126-46-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / d(4)-methanol / 2 h / 20 °C 2.1: potassium tert-butylate 2.2: gold nanoparticles supported on polytetrafluoroethylene / 0.13 h View Scheme

methanol (67-56-1) + 4-chlorobenzaldehyde methyl hemiacetal (55685-75-1) → 4-chlorobenzaldehyde (104-88-1)

Conditions	Yield
With potassium tert-butylate In d(4)-methanol at 20℃; for 2h; Equilibrium constant;

Upstream product

• 67-56-1 methanol 
• 104-88-1 4-chlorobenzaldehyde 
• 27704-37-6 2,2,2-trichloro-1-(4-chlorophenyl)ethanone 
• 106-39-8 bromochlorobenzene 

Downstream Products

• 67-56-1 methanol 
• 104-88-1 4-chlorobenzaldehyde 
• 1126-46-1 Methyl 4-chlorobenzoate 

Relevant academic research and scientific papers

PTFE supported gold nanoparticles as photocatalysts for oxidative esterification of aldehydes

Homogeneous, small gold nanoparticles (d = 1.87 nm) have been prepared by photochemical reduction of HAuCl4 in the presence of Irgacure 2959 under high power UV irradiation at 365 nm produced by a LED source. These particles have been deposited on PTFE microbeads (d = 200 μm) and evaluated for the catalysis of the oxidative esterification of aldehydes in the presence of H2O2. Under green light (λ ≈ 530 nm) and repeated addition of H2O2, the catalytic system is accelerated and achieves complete conversions in minutes. Furthermore the catalyst can be recycled ten times consecutively without any activity loss by adding a step for AuNP recycling. The mechanism of the reaction follows a zero rate order, and Hammett free energy relationships for substituted benzaldehydes afforded a positive ρ value (ρ = 2.35) demonstrating that the initial hemiacetalisation equilibrium (ρ = 2.31) is the rate determining step. Kinetics data are in agreement with an Eley-Rideal type mechanism and permits proposing a reaction mechanism.

Transition-metal-free transformation of aryl bromides into aromatic esters and amides via aryl trichloromethyl ketones

A variety of aryl bromides have been treated with Mg and then chloral, followed by tBuOCl and subsequently alcohols or amines to produce the corresponding aromatic esters or amides in good yields via the formation of aryl trichloromethyl ketones as intermediates. These reactions are examples of a transition-metal-free one-pot preparation of aromatic esters and amides from aryl bromides. Aryl bromides have been treated with Mg and then chloral, followed by tBuOCl or tBuOCl with I2 as an additive, and subsequently alcohols or amines to form the corresponding aromatic esters and aromatic amides via aryl trichloromethyl ketones as intermediates. Copyright

Electrolytic reduction of carbonyl compounds in methanol-benzene and methanol-dioxane solutions

Specific features of polarographic analysis of aldehydes and ketones in media with low dielectric constant ε (6.4-32.6) were revealed. These are a decrease in the limiting currents caused by the reaction of depolarizers with methanol and dependence of the half-wave potentials on the system composition.