80767-12-0

Basic information

• Product Name: Benzenemethanol, 4-hydroxy-, a-acetate
• Synonyms: 4-hydroxybenzyl acetate;4-Oxy-11-acetoxy-1-methyl-benzol;4-Acetoxymethyl-phenol;(4-Oxy-benzyl)-acetate;acetic acid 4-hydroxy-benzyl ester;4-acetoxymethylphenol
• CAS NO: 80767-12-0
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Mol File: 80767-12-0.mol

Chemical Properties

• Melting Point: 50 °C
• Boiling Point: 272.2±15.0 °C(Predicted)
• Density: 1.181±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzenemethanol, 4-hydroxy-, a-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, 4-hydroxy-, a-acetate(80767-12-0)
• EPA Substance Registry System: Benzenemethanol, 4-hydroxy-, a-acetate(80767-12-0)

Safety Data

• Hazardous Substances Data: 80767-12-0(Hazardous Substances Data)

Upstream product

• 623-05-2 (4-hydroxyphenyl)methanol 
• 64-19-7 acetic acid 
• 108-05-4 vinyl acetate 
• 2937-64-6 4-(acetyloxy)benzyl acetate 
• 65753-93-7 N-methyl-2-dimethylamino-acetohydroxamic acid 
• 115287-30-4 Acetic acid 4-trimethylsilanyloxy-benzyl ester 
• 75-36-5 acetyl chloride 
• 123-08-0 4-hydroxy-benzaldehyde 
• 141-78-6 ethyl acetate 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 106-44-5 p-cresol 
• 116748-06-2 (4-(hydroxymethyl)phenoxy)(tert-butyl)diphenylsilane 
• 116748-05-1 4-(tert-butyldiphenylsilyloxy)benzaldehyde 
• 108-24-7 acetic anhydride 

Downstream Products

• 5355-17-9 4-hydroxybenzyl methyl ether 
• 77094-90-7 3-(4-hydroxyphenyl)-2-ethoxycarbonyl-propionic acid ethyl ester 
• 112621-27-9 2-(4-hydroxybenzyl)-2-methyl-1,3-cyclopentanedione 
• 120677-37-4 4-(4-Ethyl-phenoxymethyl)-phenol 
• 53565-75-6 4-(phenylimino-methyl)-phenol 
• 124389-51-1 4-[(Benzyl-dodecyl-amino)-methyl]-phenol 
• 112621-26-8 2-(4-hydroxybenzyl)cyclohexane-1,3-dione 
• 55116-31-9 1-(azidomethyl)-4-hydroxybenzene 
• 45966-19-6 4-((ethylamino)methyl)phenol 
• 941282-79-7 acetic acid 1-(2-hydroxy-ethoxy)-4-oxo-cyclohexa-2,5-dienylmethyl ester 
• 881181-55-1 acetic acid 4-oxo-1-(2-oxoethoxy)cyclohexa-2,5-dienylmethyl ester 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 1092474-62-8 4-hydroxybenzyl octanoate 
• 848245-33-0 2-(4-hydroxy-benzyl)-2-methoxy-malonic acid dimethyl ester 

Relevant articles and documents

Lipase-mediated selective acetylation of primary alcohols in ethyl acetate

An environmental friendly process to selectively acetylate primary alcohols was demonstrated. The esterification process consists of treatment of a primary alcohol in the presence of immobilized C. antarctica lipase (Novozyme-435) in ethyl acetate at room temperature. Primary alcohols were acetylated in the presence of secondary alcohols and phenols.

Gastrodin production process

Disclosed is a gastrodin production process comprising the preparation of acetoxymethyl phenol, the preparation of pentacetyl gastrodin, and the preparation and refining of gastrodin, including: stirring hydroxybenzyl alcohol, glacial acetic acid and ethy

Decarboxylative Csp3-Csp3 coupling for benzylation of unstable ketone enolates: Synthesis of: P -(acylethyl)phenols

A new decarboxylative Csp3-Csp3 coupling approach for the benzylation of ketone enolates has been developed. A variety of raspberry ketone derivatives were conveniently synthesized in good to excellent yields under mild conditions. A crossover reaction shed light on the mechanism of this tandem reaction.

Syntheses of methylated catechins and theaflavins using 2-nitrobenzenesulfonyl group to protect and deactivate phenol

An efficient and versatile synthetic method for labile polyphenols was established using 2-nitrobenzenesulfonate (Ns) as a protecting group for phenol. This methodology provides regio-and stereoselective access to a range of methylated catechins, such as methylated epigallocatechin gallates, that are not readily available from natural sources. In addition, biomimetic synthesis of theaflavins from catechins was accomplished using Ns protection to minimize undesired side reactions of electron-rich aromatic rings during oxidation, enabling construction of the complex benzotropolone core in a single-step oxidative coupling reaction. Availability of these compounds will aid detailed structure-biological activity relationship studies of catechins.

Efficient approach for the chemoselective acetylation of alcohols catalyzed by a novel metal oxide nanocatalyst CuO-ZnO

A new method has been developed for the chemoselective acetylation of alcohols with acetic anhydride in the presence of phenols using a novel, recyclable CuO-ZnO nanocatalyst. The catalyst was synthesized using the co-precipitation method and characterized by N2 adsorption-desorption, X-ray diffraction, scanning electron microscopy, transmission electron microscopy and energy dispersion scanning analyses. Furthermore, this catalyst could be recycled up to six times without significant loss in its activity.

Kinetics of self-immolative degradation in a linear polymeric system: Demonstrating the effect of chain length

We describe here a study demonstrating that the degradation time of self-immolative linear polymers is dependent on chain length. These materials are unique relative to most degradable polymers, in that they undergo end-to-end depolymerization in response to the cleavage of an end-cap. Although one of their cited attributes is a dependence of their degradation time on chain length, no conclusive study has been conducted to demonstrate and study this effect. In this work, using a linear self-immolative polymer backbone derived from alternating 4-hydroxybenzyl alcohol and N,N′-dimethylethylenediamine based spacers, we show that there is a proportional relationship between chain length and depolymerization time. This is first accomplished using a series of oligomers synthesized using a convergent, iterative route and then applied to the polydisperse case on a set of polymers displaying varying molecular weights. We also report the first development and validation of a self-immolative degradation model relating monomer kinetics to polymer degradation and show its application in explaining oligomeric and polymeric degradation profiles.

Characterization of novel Cs and K substituted phosphotungstic acid modified MCM-41 catalyst and its catalytic activity towards acetylation of aromatic alcohols

TheMCM-41 supported Cs2.5H0.5PW12O 40 and K2.5H0.5PW12O40 salts were synthesized by incipient wetness impregnation method. The solids were characterized by N2 adsorption-desorption isotherms, FTIR, XRD, and temperature programmed desorption, etc. This catalyst has been found to exhibit excellent activity for acetylation of phenolic compounds. The catalyst is stable and reusable giving 96% conversion with 100% selectivity towards acetate products. Indian Academy of Sciences.

H6GeMo10V2O40·16H 2O nanoparticles prepared by hydrothermal method: A new and reusable heteropoly acid catalyst for highly efficient acetylation of alcohols and phenols under solvent-free conditions

A new Keggin-type heteropoly acid, namely decamolybdodivanadogermanic acid (H6GeMo10V2O40·16H 2O), with nanosized particles (5-8 nm), has been synthesized by a hydrothermal method and characterized by elemental analysis, thermogravimetric analysis (TGA), powder X-ray diffractometry (XRD), Fourier-transform infrared spectroscopy (FTIR), UV-Visible spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM) and potentiometric titration. H6GeMo10V2O40·16H 2O revealed high catalytic activity for acetylation of various alcohols and phenols with acetic anhydride at room temperature (298 ± 2 K) and under solvent-free conditions. The catalyst can be easily recovered and used repeatedly for five cycles with a slight loss of activity. The catalytic activity of H6GeMo10V2O40· 16H2O was higher than that of other Keggin-type heteropoly acids, such as H3PW12O40, H3PMo 12O40 and H4SiW12O40.

One-pot sequence for reductive-acetylation of carbonyl compounds with (N-methylimidazole)(tetrahydroborato)zinc complex

Reductive-acetylation of variety of aliphatic and aromatic aldehydes and ketones, α,β-unsaturated carbonyl compounds are examined efficiently with (N-methylimidazole)(tetrahydroborato)zinc complex, [Zn(BH4) 2(nmi)], under mild condition in THF at room temperature or reflux conditions. The corresponding acetates were obtained in excellent yields (90-98 %).

Spinel-type zinc aluminate (ZnAl2O4) nanoparticles prepared by the co-precipitation method: A novel, green and recyclable heterogeneous catalyst for the acetylation of amines, alcohols and phenols under solvent-free conditions

Zinc aluminate (ZnAl2O4) nanoparticles with an average particle size of about 8 nm were easily prepared by the co-precipitation method using aqueous ammonia solution as the precipitating agent. This nanosized spinel-type oxide was characterized by TGA, XRD, FT-IR, TEM, and surface area measurement and used as the heterogeneous catalyst for the acetylation reaction. Efficient acetylation of various amines, alcohols and phenols was carried out over ZnAl2O4 nanoparticles using acetic anhydride and/or acetyl chloride as the acetylating agents at room temperature without the use of a solvent. The method is highly selective, allowing the alcoholic hydroxyl group to be protected while the phenolic hydroxyl group remains intact, and the amine group can be acetylated in the presence of the hydroxyl group. This method is fast and has a high yield. It is also clean, safe, cost effective, compatible with substrates that have other functional groups and very suitable for practical organic synthesis. In addition, the catalyst can be reused without significant loss of activity. Indeed, the catalytic activity of the ZnAl2O4 nanoparticles is higher than that of bulk ZnAl2O4.