2503-23-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxy-5-Methoxybenzeneethanol is used as a key intermediate for the synthesis of Dihydrobenzofurans, which are the key structural elements of neolignans. Neolignans have been found to possess various biological activities, including anti-inflammatory, anti-viral, and anti-cancer properties, making them valuable compounds for the development of new pharmaceutical agents.
Used in Organic Synthesis:
2-Hydroxy-5-Methoxybenzeneethanol is used as a versatile building block in organic synthesis for the preparation of a wide range of organic compounds, including natural products, pharmaceuticals, and agrochemicals. Its unique structure allows for various chemical reactions, such as oxidation, reduction, and coupling, enabling the synthesis of diverse target molecules.

Upstream product

• 7417-19-8 2-(2,5-dimethoxyphenyl)ethanol 
• 1758-25-4 (2,5-dimethoxyphenyl)acetic acid 
• 736985-50-5 2-allyl-1-(tert-butyldimethylsilyloxy)-4-methoxybenzene 
• 150-76-5 4-methoxy-phenol 
• 584-82-7 2-allyl-4-methoxyphenol 
• 13391-35-0 allyl (4-methoxyphenyl) ether 
• 783332-86-5 2-[2-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-phenyl]-ethanol 
• 2503-24-4 5-methoxybenzofuran-2(3H)-one 

Downstream Products

• 4082-30-8 2-(2'-hydroxyethyl)-1,4-benzoquinone 
• 40492-52-2 2,3-dihydrobenzofuran-5-ol 

Relevant academic research and scientific papers

A biomimetic approach to dihydrobenzofuran synthesis

A method for an acid-catalyzed construction of dihydrobenzofuran heterocycles (14) from 2-(2′-hydroxyethyl)quinone precursors 10 is presented. The putative oxonium ion intermediate 17 formed by an intramolecular hydroxyl cyclization followed by dehydration is reduced in situ by an added dihydroquinone source. Good to excellent yields of cyclized products are realized in all cases except for highly electron deficient systems, and these suffer reduction prior to oxonium ion formation. All products are monomeric and derived from a two-electron transfer except for 10g, which affords the dimeric dihydrobenzofuran. The amount of cyclization or reduction product is governed by the HOMO/LUMO gap between the quinone substrate and the dihydroquinone additive, and the product distribution can be adjusted by modifying the electronic properties of the added reducing agent.

Hydroxyl-Directed Regioselective Monodemethylation of Polymethoxyarenes

Methoxyl groups ortho to β-hydroxyethyl or γ-hydroxypropyl substituents in polymethoxybenzene derivatives were regioselectively demethylated with sodium thioethoxide in N,N-dimethylformamide.Methoxydihydrobenzofurans or methoxychromans were produced by cyclization of the monodemethylated β-hydroxyethyl or γ-hydroxypropyl derivatives, respectively.