4-Methoxybenzyl alcohol

Base Information

• Chemical Name: 4-Methoxybenzyl alcohol
• CAS No.: 105-13-5
• Deprecated CAS: 185532-75-6
• Molecular Formula: C8H10O2
• Molecular Weight: 138.166
• Hs Code.: 29094990
• European Community (EC) Number: 203-273-6
• NSC Number: 2151
• UNII: 7N6XGV3U49
• DSSTox Substance ID: DTXSID6044357
• Nikkaji Number: J4.028B
• Wikipedia: Anisyl_alcohol
• Wikidata: Q548873
• RXCUI: 1424668
• Metabolomics Workbench ID: 46442
• ChEMBL ID: CHEMBL294431
• Mol file: 105-13-5.mol

Synonyms:4-methoxybenzyl alcohol;anisalcohol;anisyl alcohol;benzenemethanol, ar-methoxy-;p-methoxybenzyl alcohol;para-methoxybenzyl alcohol

Chemical Property of 4-Methoxybenzyl alcohol

Chemical Property:

• Appearance/Colour: clear colourless to yellowish liquid after melting
• Vapor Pressure: 0.00679mmHg at 25°C
• Melting Point: 22-25 °C(lit.)
• Refractive Index: n20/D 1.544(lit.)
• Boiling Point: 259 °C(lit.)
• PKA: 14.43±0.10(Predicted)
• Flash Point: 230 °F
• PSA: 29.46000
• Density: 1.113 g/mL at 25 °C(lit.)
• LogP: 1.18750
• Storage Temp.: Store at RT.
• Solubility.: alcohol: freely soluble
• Water Solubility.: insoluble
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 138.068079557
• Heavy Atom Count: 10
• Complexity: 85.3

Purity/Quality:

99% ^*data from raw suppliers

4-Methoxybenzyl alcohol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-63-62-41-37/38-20/21/22
• Safety Statements: 26-36-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: COC1=CC=C(C=C1)CO
• Uses: 1. 4-Methoxybenzyl alcohol mainly used in floral flavor with fragrance flavor, such as hawthorn flowers, jasmine, acacia, shy flowers, acacia, lilac, lily of the valley, violet, magnolia, sunflower, daffodils and so on. It can also be used for the need for chypre spices with vanilla flavor to coordinate the aroma and increase the aroma of beans. It can also be used for chocolate, cocoa and fresh fruit flavor. 2. GB 2760-1996 provides as allowable food flavors. It is mainly used for the preparation of vanilla, chocolate, cocoa, almonds, peaches and other flavor. 3. It is used for the preparation of drugs and spices. 4. It is used as pharmaceutical intermediates. 5. 4-Methoxybenzyl alcohol has a slightly sweet aroma of anise, commonly used in the preparation of jasmine, lilac and other flavors, suitable for deployment of perfume. The goods are allowable food spices provided in China's GB2760-86. It is mainly used to formulate the flavor of vanilla, chocolate, cocoa, almonds and peaches. It can also be used in organic synthesis and as a solvent. 6. It is used as moxonidine intermediates. 7. It is alcohol synthesis spices. It is mainly used as the blending spices of jasmine, cloves, fragrant peas, gardenia and other flavors for perfume and other cosmetics. 8. It can provide the temporary protection for the carbohydrate anti-OH-group. 4-Methoxybenzyl Alcohol is used in the preparation of semiconductors, nanosheets and nanocrystals. Also is used as a reagent for various chemical organic reactions such as in the synthesis of quinolines. It is used as a fragrance and flavorant. It is used to study the photo catalytic oxidation of 4-methoxybenzyl alcohol to p-anisaldehyde. 4-Methoxybenzyl Alcohol is used in the preparation of semiconductors, nanosheets and nanocrystals. Also is used as a reagent for various chemical organic reactions such as in the synthesis of quinolin es. 4-Methoxybenzyl alcohol was used to study the photocatalytic oxidation of 4-methoxybenzyl alcohol to p-anisaldehyde.
• Production method: It is obtained through the anisaldehyde reduction. The anise, formaldehyde and sodium hydroxide are subject to Cannizzaro reaction in the ethanol to generate p-methoxybenzyl alcohol. After distilling to recycle the ethanol, the resulting oil layer is extracted with benzene, acidified with acetic acid, neutralized by sodium hydrogencarbonate to a weak basicity, washed with water to neutral, then distillation to recover benzene with the residue subjecting to distillation under reduced pressure to obtain p-methoxy Benzyl alcohol. In methanol solution, apply potassium hydroxide solution for treatment of the mixture of anisaldehyde and formaldehyde, getting mixture of anole alcohol and formic acid. Apply benzene extraction and then purify through distillation. Use platinum as a catalyst and ferrous chloride as a reductant, obtain it through anisidine hydrogenation.

Technology Process of 4-Methoxybenzyl alcohol

There total 403 articles about 4-Methoxybenzyl alcohol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4-methoxy-benzaldehyde (123-11-5) → 4-methoxybenzoic acid (100-09-4) + 4-Methoxybenzyl alcohol (105-13-5)

Guidance literature:

With Ximenia american; In aq. phosphate buffer; water; at 30 ℃; for 72h; pH=7; Enzymatic reaction;

DOI:10.1016/j.mcat.2017.11.033

Reference yield: 63.0%

4-methoxybenzyltri-n-butylstannane (74260-40-5) → 4-methoxy-benzaldehyde (123-11-5) + 4-methoxybenzoic acid (100-09-4) + 4-Methoxybenzyl alcohol (105-13-5)

Guidance literature:

With C₂H₂Cl₂F₃O₂V; oxygen; In tert-butyl alcohol; at 50 ℃; for 72h;

DOI:10.1016/S0040-4039(01)00083-1

Reference yield: 35.0%

p-methoxybenzyl chloride (824-94-2) → 4-methoxy-benzaldehyde (123-11-5) + 4-methoxybenzoic acid (100-09-4) + 4-Methoxybenzyl alcohol (105-13-5)

Guidance literature:

With potassium hydroxide; cetyltrimethylammonim bromide; potassium nitrate; In water; for 0.25h; pH=10 - 11; Reflux;

DOI:10.1080/00397910802323080

upstream raw materials:

4-methoxyphenylacetamide

p-methoxybenzyl acetate

methyl 4-methoxybenzoate

methanol

Downstream raw materials:

2-(4-methoxybenzylamino)pyridine

carbonic acid ethyl ester-(4-methoxy-benzyl ester)

9-(4-methoxybenzyl)-9H-fluorene

4-methoxybenzyl phenylcarbamate

Refernces

Optically Active Organoiron Complexes in Synthesis. An Enantioface Selective 3-Hydroxypropionate-2,3-Dication Equivalent

10.1016/S0040-4039(00)91888-4

The research focuses on the application of optically active organoiron complexes as chiral 3-hydroxypropionate-2,3-dication equivalents in asymmetric synthesis. The purpose of the study was to demonstrate the enantioface-selective synthesis of 2,3-disubstituted 3-hydroxypropionates using a series of transformations involving the addition of nucleophiles to organoiron complexes, followed by redox-promoted carboxylation. The key chemicals used in the process include Fp(q^2-1,2-dimethoxyethylene)BF, (R,R)-butane-2,3-dial, lithium dimethylcuprate, p-methoxybenzyl alcohol, ethyl Grignard, and various reagents for oxidation and deprotection steps. The conclusions drawn from the research indicate that the organoiron complexes can serve as effective enantioface-selective equivalents, leading to the synthesis of optically active compounds such as (2R,3S)-methyl-2-methyl-3-p-methoxybenzyloxypentanoate and enantio-pure sitophilate, the latter being the enantiomer of the granary weevil aggregation pheromone. The study also suggests potential for further exploration in the preparation of syn- or anti-diastereomers of β-hydroxyesters using this methodology.