6161-96-2

Usage

Uses

Used in Pharmaceutical Industry:
Benzenemethanol, 2-hydroxy-, a-acetate is used as an intermediate in the synthesis of 2-Hydroxymethyl Atomoxetiene (H946705), a metabolite of Atomoxetiene (A791400). Atomoxetiene is a norepinephrine reuptake inhibitor, which is a type of medication used to treat attention deficit hyperactivity disorder (ADHD) and other conditions related to attention and focus. Benzenemethanol, 2-hydroxy-, a-acetate plays a crucial role in the development of these medications due to its involvement in the synthesis process.

Upstream product

• 1575-87-7 o-acetoxybenzyl acetate 
• 90-01-7 salicylic alcohol 
• 108-24-7 acetic anhydride 
• 52727-97-6 2-Acetoxybenzyltosylat 
• 932-30-9 2-Hydroxybenzylamine 
• 64-19-7 acetic acid 
• 5663-67-2 2-acetoxybenzaldehyde 
• 141-78-6 ethyl acetate 
• 1058648-91-1 2-[(ethoxymethoxy)methyl]phenol 
• 1058648-87-5 2-[(methoxymethoxy)methyl]phenol 
• 75-36-5 acetyl chloride 
• 108-05-4 vinyl acetate 
• 18885-85-3 2-phenyl-4H-benzo-1,3,2-dioxaborine 

Downstream Products

• 130413-05-7 benzenemethanol, 2-[(tetrahydro-2H-pyran-2-yl)oxy]-, acetate 
• 124389-46-4 2-(4-Ethyl-phenoxymethyl)-phenol 
• 124389-54-4 2-(2-Hydroxy-benzyl)-2-methyl-malonic acid diethyl ester 
• 55116-30-8 2‐(azidomethyl)phenol 
• 124389-50-0 2-[(Benzyl-ethyl-amino)-methyl]-phenol 
• 4992-02-3 o-dimethylaminomethylphenol 
• 494-12-2 flavan 
• 53565-75-6 4-(phenylimino-methyl)-phenol 
• 1029608-20-5 C₁₇H₁₈O₂ 
• 1029608-21-6 C₁₈H₂₀O₄ 
• 1029608-22-7 C₁₈H₂₀O₄ 
• 1029608-17-0 C₁₆H₁₆O₂ 
• 1026599-22-3 C₁₇H₁₈O₃ 

Relevant academic research and scientific papers

Generation and hetero-Diels-Alder reactions of an o-quinone methide under mild, anionic conditions: Rapid synthesis of mono-benzannelated spiroketals

Deprotonation of o-hydroxybenzyl acetate with iPrMgCl provides a method of generating an o-quinone methide under mild, anionic conditions, such that highly sensitive exo-enol ethers can be employed as 2π partners in hetero-Diels-Alder reactions

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.

Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry

Background: The ionic liquid triethylammonium acetate (TEAA) was found to be an efficient solvent in the acetylation of alcohols, amines, oximes and thiols to their corresponding acetyl compounds using only a 10% excess of acetic anhydride under mild conditions. Moreover TEAA is not only an inexpensive and recyclable solvent but also an anomeric selective catalyst in the per-O-acetylation of sugar moieties. Methods: Simple and effective organic synthesis protocols were provided for the selective acetylation of several substrates. The products were fully characterized by 1H and 13C NMR spectroscopy and the anomeric ratios were obtained from the 1H spectra. Results: Structurally diverse alcohols, phenols, thiols, amines, carbohydrates and oximes underwent acylation under mild conditions by this procedure to provide the corresponding acetates in excellent yields. TEAA ionic liquid is unique in its capability to act as both, solvent and high selective catalyst. As expected, the reaction proceeds with high b anomeric selectivity for sugars derivatives. Moreover, the ionic liquid was regenerated, recycled and reused for three times without apparent loss of reactivity and selectivity in all cases. Conclusions: The present procedure provides a powerful and versatile acylation method for alcohols, phenols, thiols, amines, oximes and carbohydrates. This protocol is endowed with several unique merits: selectivity, cost-efficiency, atom-economy and mild reaction conditions tolerable to acid sensitive functionalities. With these features, this method may be considered as a better alternative for the acetylation of a wide range of substrates.

Copper(I)-catalyzed hydroalkoxylation/hydrogen-bonding-induced asymmetric hetero-diels-alder cycloaddition cascade: An approach to aromatic spiroketals

One thing leads to another: Bis(benzannelated) 5,6-spiroketal skeletons can be constructed by an efficient cascade process involving an unprecedented CuI-catalyzed intramolecular alkyne hydroalkoxylation and an asymmetric hetero-Diels-Alder cyc

Solvent free, highly chemoselective N and O-acylation on silica and silica magnesium oxide: A recyclable solid surface

Silica or silica/magnesium oxide mixed surface mediates the N and O-acylation, benzoylation or sulfonylation of hosts of substrates under solvent free conditions at ambient temperature with high chemoselectivity.

A green method for selective acetylation of primary alcohols using ethyl acetate and solid potassium carbonate

A simple and selective acetylation of primary alcohols in the presence of other reactive functionalities such as secondary alcohol, phenol, acetonide and amine is described using mild ethyl acetate as the acetyl-transfer agent and solid potassium carbonate as the catalyst.

Microwave-assisted rapid and efficient deprotection and direct esterification and silylation of MOM and EOM ethers catalyzed by [Hmim][HSO 4] as a Bronsted acidic ionic liquid

1-Methylimidazolium hydrogensulfate, [Hmim] [HSO4], a Bronsted acidic room temperature ionic liquid, is used as a catalyst and reaction medium for facile and ecofriendly deprotection of methoxymethyl (MOM) and ethoxymethyl (EOM) ethers to their corresponding alcohols under thermal conditions (Δ) and microwave irradiation (MW). Furthermore, one-pot interconversion to the respective acetates and trimethylsilyl (TMS) ethers was also achieved. Springer-Verlag 2010.

An approach to benzannelated [5,6]-spiroketals

Heating a variety of 2-hydroxybenzyl acetates bearing a range functional groups on the 4- or 5-position of the aromatic ring at 100°C in neat γ-methylene-γ-butyrolactone (1.0 M) for 20 hours gives a series of benzannelated [5,6]-spiroketals in 75-89% yiel

o-Quinone methide based approach to isoflavans: application to the total syntheses of equol, 3′-hydroxyequol and vestitol

A concise strategy is developed for the synthesis of isoflavans employing a Diels-Alder reaction between o-quinone methides and aryl-substituted enol ethers followed by reductive cleavage of the acetal group. The method is extended towards the total syntheses of equol, 3′-hydroxyequol and vestitol.

Selective acetylation of alcohols and amines with ethyl acetate in the presence of H6[PMo9V3O40] as the catalyst

Acetylation of various alcohols and benzyl amine was tested in the presence of H6[PMo9V3O40], a mixed addenda heteropolyacid, in ethyl acetate under reflux condition. Phenols and anilines are not affected under the reaction conditions. Selective transestrification of alcohols can be achieved in the presence of phenol and aniline derivatives using this method. Springer-Verlag 2007.