1-(3-hydroxy-4-methoxyphenyl)-2-hydroxyethanone

Base Information

• Chemical Name: 1-(3-hydroxy-4-methoxyphenyl)-2-hydroxyethanone
• CAS No.: 90536-46-2
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.176
• Mol file: 90536-46-2.mol

Synonyms:1-(3-hydroxy-4-methoxyphenyl)-2-hydroxyethanone

Chemical Property of 1-(3-hydroxy-4-methoxyphenyl)-2-hydroxyethanone

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3-hydroxy-4-methoxyphenyl)-2-hydroxyethanone

There total 9 articles about 1-(3-hydroxy-4-methoxyphenyl)-2-hydroxyethanone 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:

guaiacylglycerol-β-guaiacyl ether (7382-59-4) → 1-(3-hydroxy-4-methoxyphenyl)ethane-1,2-diol (40979-91-7) + 1-(3-hydroxy-4-methoxyphenyl)-2-hydroxyethanone (90536-46-2) + vanillin (121-33-5,8014-42-4) + 2-methoxy-phenol (90-05-1)

Guidance literature:

With dihydrogen peroxide; In acetonitrile; at 80 ℃; for 3h; Reagent/catalyst;

DOI:10.33224/rrch.2020.65.11.02

Reference yield:

C15H24O4Si → 1-(3-hydroxy-4-methoxyphenyl)-2-hydroxyethanone (90536-46-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.bmc.2017.01.050

Reference yield:

ethyl 3-hydroxy-4-methoxymandelate (91971-78-7) → 1-(3-hydroxy-4-methoxyphenyl)-2-hydroxyethanone (90536-46-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium carbonate / acetone / 0.08 h / Inert atmosphere

1.2: Reflux; Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 2 h / Inert atmosphere; Reflux

3.1: triethylamine; dmap / dichloromethane / 20 °C / Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / 0 °C / Inert atmosphere

5.1: hydrogen; palladium 10% on activated carbon / methanol / 16 h / 20 °C / 1551.49 Torr / Autoclave

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone;

DOI:10.1016/j.bmc.2017.01.050

upstream raw materials:

2-acetoxy-1-(3-acetoxy-4-methoxy-phenyl)-ethanone

1-(3-acetoxy-4-methoxy-phenyl)-2-diazo-ethanone

ethyl 3-hydroxy-4-methoxymandelate

1-(3-benzyloxy-4-methoxyphenyl)ethane-1,2-diol

Refernces

• 1、 Cardinal, Sébastien,Paquet-C?té, Pierre-Alexandre,Azelmat, Jabrane,Bouchard, Corinne,Grenier, Daniel,Voyer, Normand. "Synthesis and anti-inflammatory activity of isoquebecol". . p. 2043 - 2056. Retrieved 2017/03/23.