1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-hydroxyethanone

Base Information

• Chemical Name: 1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-hydroxyethanone
• CAS No.: 583860-52-0
• Molecular Formula: C10H10O4
• DSSTox Substance ID: DTXSID30402937
• Wikidata: Q82206464
• Mol file: 583860-52-0.mol

Synonyms:583860-52-0;1-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-hydroxyethanone;1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-2-hydroxyethanone;CHEMBRDG-BB 5785240;Oprea1_394172;SCHEMBL4831672;DTXSID30402937;MFCD03059058;STK109787;AKOS005398402;BS-38234

Chemical Property of 1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-hydroxyethanone

Chemical Property:

• Vapor Pressure: 2.85E-06mmHg at 25°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 216

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2=C(O1)C=CC(=C2)C(=O)CO

Technology Process of 1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-hydroxyethanone

There total 2 articles about 1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-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:

2-bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethanone (4629-54-3) → 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-hydroxyethan-1-one (583860-52-0)

Guidance literature:

With lithium formate; In ethanol; water; for 12h; Reflux;

DOI:10.1016/j.ejmech.2020.112218

Reference yield:

1,4-benzodioxan-6-yl methyl ketone (2879-20-1) → 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-hydroxyethan-1-one (583860-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(ll) bromide / chloroform / 20 h / 70 °C

2: lithium formate / ethanol; water / 12 h / Reflux

With lithium formate; copper(ll) bromide; In ethanol; chloroform; water;

DOI:10.1016/j.ejmech.2020.112218

Reference yield:

1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-hydroxyethan-1-one (583860-52-0) → 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-phenylethanone (18212-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

2: bis(tricyclohexylphosphine)nickel(II) dichloride; sodium t-butanolate / N,N-dimethyl-formamide; toluene / 0.67 h / 100 °C / Inert atmosphere

With bis(tricyclohexylphosphine)nickel(II) dichloride; triethylamine; sodium t-butanolate; In dichloromethane; N,N-dimethyl-formamide; toluene; 2: Suzuki-Miyaura coupling;

DOI:10.1039/c1cc11193k

upstream raw materials:

1,4-benzodioxan-6-yl methyl ketone

2-bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethanone

Downstream raw materials:

1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-phenylethanone