6766-82-1

Basic information

• Product Name: Phenol, 2,6-dimethoxy-4-propyl-
• Synonyms: Phenol, 2,6-dimethoxy-4-propyl-;4-PROPYL-2,6-DIMETHOXYPHENOL;2,6-DIMETHOXY-4-PROPYLPHENOL;4-Propylsyringol;Syringylpropane
• CAS NO: 6766-82-1
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.2429
• Mol File: 6766-82-1.mol

Chemical Properties

• Boiling Point: 300.8°Cat760mmHg
• Flash Point: 135.7°C
• Appearance: /
• Density: 1.059g/cm³
• Vapor Pressure: 0.000613mmHg at 25°C
• Refractive Index: 1.513
• CAS DataBase Reference: Phenol, 2,6-dimethoxy-4-propyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 2,6-dimethoxy-4-propyl-(6766-82-1)
• EPA Substance Registry System: Phenol, 2,6-dimethoxy-4-propyl-(6766-82-1)

Safety Data

• Hazardous Substances Data: 6766-82-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Phenol, 2,6-dimethoxy-4-propylis used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the development of new drugs, particularly those targeting specific diseases and conditions.
Used in Chemical Synthesis:
In the chemical industry, Phenol, 2,6-dimethoxy-4-propylis used as a versatile building block for the synthesis of a wide range of organic compounds. Its reactivity and functional groups make it suitable for various chemical reactions, leading to the production of different chemicals with diverse applications.
Used in Flavor and Fragrance Industry:
Phenol, 2,6-dimethoxy-4-propylis used as a component in the creation of natural flavors and fragrances. Its unique aroma and taste profile contribute to the development of new and innovative products in the flavor and fragrance market.
Used in Antioxidant Applications:
Due to its phenolic nature, Phenol, 2,6-dimethoxy-4-propylexhibits antioxidant properties, making it a potential candidate for use in the food and cosmetic industries. It can help prevent oxidation and spoilage, thereby extending the shelf life of products and maintaining their quality.
Used in Material Science:
Phenol, 2,6-dimethoxy-4-propylcan be utilized in the development of advanced materials, such as polymers and composites, due to its chemical reactivity and structural properties. It can be incorporated into the synthesis of new materials with improved mechanical, thermal, and electrical properties.

InChI:InChI=1/C11H16O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h6-7,12H,4-5H2,1-3H3

Synthetic route

4-allyl-2,6-dimethoxyphenol (6627-88-9) → 4-n-propylsyringol (6766-82-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; Ambient temperature;	89%
With palladium 10% on activated carbon; hydrogen In methanol at 60℃; under 30003 Torr; for 16h;	83%
With palladium on activated charcoal; ethanol Hydrogenation;

1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one (5650-43-1) → 4-n-propylsyringol (6766-82-1)

Conditions	Yield
With boron trifluoride diethyl etherate; sodium cyanoborohydride In tetrahydrofuran at 20℃; for 12h;	80%
With hydrogenchloride; amalgamated zinc

Upstream product

• 22805-53-4 2-acetoxy-1,3-dimethoxy-5-propyl-benzene 
• 6627-88-9 4-allyl-2,6-dimethoxyphenol 
• 5650-43-1 1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one 
• 29540-11-2 4-allyl-2,6-dimethoxyphenyl acetate 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 10061-52-6 1-(3,5-dimethoxy-4-hydroxyphenyl)-1-propanol 

Downstream Products

• 860724-84-1 3-hydroxy-2,4-dimethoxy-6-propyl-benzaldehyde 
• 530-55-2 2,6-dimethoxy-p-quinone 
• 861383-97-3 5-propylbenzene-1,2,3-triol 
• 22805-53-4 2-acetoxy-1,3-dimethoxy-5-propyl-benzene 
• 41564-88-9 1-(3',4',5'-trimethoxyphenyl)propane 
• 24760-60-9 2,6-dimethoxy-4-propylidene-2,5-cyclohexadien-1-one 
• 1240613-85-7 4-(2,6-dimethoxy-4-propylphenoxy)benzonitrile 
• 1240613-84-6 3-chloro-4-(2,6-dimethoxy-4-propylphenoxy)benzonitrile 
• 5650-43-1 1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one 
• 1678-92-8 propylcyclohexane 
• 2785-87-7 2-methoxy-4-n-propylphenol 
• 103-65-1 phenylpropane 
• 55136-70-4 3-methoxy-5-propylphenol 
• 71-43-2 benzene 

Relevant articles and documents

Controlling lignin solubility and hydrogenolysis selectivity by acetal-mediated functionalization

Existing lignocellulosic biomass fractionation processes produce lignin with random, interunit C-C bonds that inhibit its depolymerization and constrain its use. Here, we exploit the aldehyde stabilization of lignin to tailor its structure, functionality,

Efficient demethylation of aromatic methyl ethers with HCl in water

A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could be easily scaled and biorenewable 4-propylguaiacol from wood and clove oil could also be applied as a feedstock. Greenness of the developed methodversusstate-of-the-art demethylation reactions was assessed by performing a quantitative and qualitative Green Metrics analysis. Versatility of the method was shown on a variety of aromatic methyl ethers containing (biorenewable) substrates, yielding up to 99% of the corresponding aromatic alcohols, in most cases just requiring simple extraction as work-up.

Aromatic compound hydrogenation and hydrodeoxygenation method and application thereof

The invention belongs to the technical field of medicines, and discloses an aromatic compound hydrogenation and hydrodeoxygenation method under mild conditions and application of the method in hydrogenation and hydrodeoxygenation reactions of the aromatic compounds and related mixtures. Specifically, the method comprises the following steps: contacting the aromatic compound or a mixture containing the aromatic compound with a catalyst and hydrogen with proper pressure in a solvent under a proper temperature condition, and reacting the hydrogen, the solvent and the aromatic compound under the action of the catalyst to obtain a corresponding hydrogenation product or/and a hydrodeoxygenation product without an oxygen-containing substituent group. The invention also discloses specific implementation conditions of the method and an aromatic compound structure type applicable to the method. The hydrogenation and hydrodeoxygenation reaction method used in the invention has the advantages of mild reaction conditions, high hydrodeoxygenation efficiency, wide substrate applicability, convenient post-treatment, and good laboratory and industrial application prospects.

Lignin Valorization by Cobalt-Catalyzed Fractionation of Lignocellulose to Yield Monophenolic Compounds

Herein, a catalytic reductive fractionation of lignocellulose is presented using a heterogeneous cobalt catalyst and formic acid or formate as a hydrogen donor. The catalytic reductive fractionation of untreated birch wood yields monophenolic compounds in up to 34 wt % yield of total lignin, which corresponds to 76 % of the theoretical maximum yield. Model compound studies revealed that the main role of the cobalt catalyst is to stabilize the reactive intermediates formed during the organosolv pulping by transfer hydrogenation and hydrogenolysis reactions. Additionally, the cobalt catalyst is responsible for depolymerization reactions of lignin fragments through transfer hydrogenolysis reactions, which target the β-O-4′ bond. The catalyst could be recycled three times with only negligible decrease in efficiency, showing the robustness of the system.

Depolymerization of lignin: Via a non-precious Ni-Fe alloy catalyst supported on activated carbon

Lignin primarily composed of methoxylated phenylpropanoid subunits is an abundant biomass that can be used to produce aromatics. Herein, a series of non-precious bimetallic Ni-Fe/AC catalysts were prepared for efficiently depolymerizing lignin. When organosolv birch lignin was used to determine the efficiency of the catalysts in methanol solvent, the Ni1-Fe1/AC (the ratio of Ni and Fe was 1 : 1) achieved the highest total yield of monomers (23.2 wt%, mainly propylguaiacol and propylsyringol) at 225 °C under 2 MPa H2 for 6 h. From GPC analysis, it is also proved that lignin was efficiently depolymerized. The Ni-Fe alloy structure was formed according to XRD, HRTEM, H2-TPR and XPS characterization. Based on the model compounds' tests, the Ni1-Fe1/AC catalyst showed high efficiency in ether bond cleavage without hydrogenation of aromatic rings which could be attributed to the synergistic effect of Ni and Fe on the alloy structure. The total yield of monomers by using the Ni1-Fe1/AC catalyst reached 39.5 wt% (88% selectivity to PG and PS) when birch wood sawdust was used as the substrate.

Lignin depolymerization to monophenolic compounds in a flow-through system

A reductive lignocellulose fractionation in a flow-through system in which pulping and transfer hydrogenolysis steps were separated in time and space has been developed. Without the hydrogenolysis step or addition of trapping agents to the pulping, it is possible to obtain partially depolymerized lignin (21 wt% monophenolic compounds) that is prone to further processing. By applying a transfer hydrogenolysis step 37 wt% yield of lignin derived monophenolic compounds was obtained. Pulp generated in the process was enzymatically hydrolyzed to glucose in 87 wt% yield without prior purification.

Isolation of functionalized phenolic monomers through selective oxidation and CO bond cleavage of the β-O-4 linkages in Lignin

Functionalized phenolic monomers have been generated and isolated from an organosolv lignin through a two-step depolymerization process. Chemoselective catalytic oxidation of β-O-4 linkages promoted by the DDQ/tBuONO/ O2 system was achieved in model compounds, including polymeric models and in real lignin. The oxidized β-O-4 linkages were then cleaved on reaction with zinc. Compared to many existing methods, this protocol, which can be achieved in one pot, is highly selective, giving rise to a simple mixture of products that can be readily purified to give pure compounds. The functionality present in these products makes them potentially valuable building blocks.

A synergistic biorefinery based on catalytic conversion of lignin prior to cellulose starting from lignocellulosic biomass

Current biomass utilization processes do not make use of lignin beyond its heat value. Here we report on a bimetallic Zn/Pd/C catalyst that converts lignin in intact lignocellulosic biomass directly into two methoxyphenol products, leaving behind the carbohydrates as a solid residue. Genetically modified poplar enhanced in syringyl (S) monomer content yields only a single product, dihydroeugenol. Lignin-derived methoxyphenols can be deoxygenated further to propylcyclohexane. The leftover carbohydrate residue is hydrolyzed by cellulases to give glucose in 95% yield, which is comparable to lignin-free cellulose (solka floc). New conversion pathways to useful fuels and chemicals are proposed based on the efficient conversion of lignin into intact hydrocarbons. This journal is

CONTINUOUS PROCESS FOR CONVERSION OF LIGNIN TO USEFUL COMPOUNDS

This specification discloses an operational continuous process to convert lignin as found in ligno-cellulosic biomass before or after converting at least some of the carbohydrates. The continuous process has been demonstrated to create a slurry comprised of lignin, raise the slurry comprised of lignin to ultra-high pressure, deoxygenate the lignin in a lignin conversion reactor over a catalyst which is not a fixed bed without producing char. The conversion products of the carbohydrates or lignin can be further processed into polyester intermediates for use in polyester preforms and bottles.

Catalytic conversion of biomass using solvents derived from lignin

We report an approach by which the hemicellulose and cellulose fractions of biomass are converted through catalytic processes in a solvent prepared from lignin into high value platform chemicals and transportation fuels, namely furfural, 5-hydroxymethylfurfural, levulinic acid and γ-valerolactone. The Royal Society of Chemistry.