4,5-Dimethoxyisobenzofuran-1(3H)-one

Base Information

• Chemical Name: 4,5-Dimethoxyisobenzofuran-1(3H)-one
• CAS No.: 4741-58-6
• Molecular Formula: C10H10 O4
• Molecular Weight: 194.187
• Hs Code.: 2932209090
• DSSTox Substance ID: DTXSID90505231
• Wikidata: Q82360197
• Mol file: 4741-58-6.mol

Synonyms:4,5-Dimethoxyisobenzofuran-1(3H)-one;4741-58-6;4,5-dimethoxyphthalide;4,5-DIMETHOXY-3H-2-BENZOFURAN-1-ONE;4,5-dimethoxy-1,3-dihydro-2-benzofuran-1-one;4,5-di-methoxyphthalide;SCHEMBL4110681;DTXSID90505231;ZXIMTZPOPPEWHU-UHFFFAOYSA-N;MFCD00126369;4,5-Dimethoxy-2-benzofuran-1(3H)-one;E84367;A914742

Chemical Property of 4,5-Dimethoxyisobenzofuran-1(3H)-one

Chemical Property:

• Melting Point: 122-123 °C
• Boiling Point: 404.2±45.0 °C(Predicted)
• PSA: 44.76000
• Density: 1.260±0.06 g/cm3(Predicted)
• LogP: 1.37420
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 228

Purity/Quality:

99%min ^*data from raw suppliers

4,5-Dimethoxyisobenzofuran-1(3H)-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(C=C1)C(=O)OC2)OC

Technology Process of 4,5-Dimethoxyisobenzofuran-1(3H)-one

There total 16 articles about 4,5-Dimethoxyisobenzofuran-1(3H)-one 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: 78.0%

carbon monoxide (201230-82-2) + (6-iodo-2,3-dimethoxyphenyl)methanol (74785-03-8) → 4,5-dimethoxyisobenzofuran-1(3H)-one (4741-58-6)

Guidance literature:

With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 50 ℃; for 60h; under 3040 Torr;

DOI:10.1021/ja00532a034

Reference yield: 64.0%

terephthalaldehyde, (623-27-8) + 2-bromomethyl-1-iodo-4,5-dimethoxybenzene (110451-87-1) → 4,5-dimethoxyisobenzofuran-1(3H)-one (4741-58-6)

Guidance literature:

terephthalaldehyde,; With palladium 10% on activated carbon; sodium carbonate; In isopropyl alcohol; at 120 ℃; for 24h; Inert atmosphere;

2-bromomethyl-1-iodo-4,5-dimethoxybenzene; With triphenylphosphine; In 1-methyl-pyrrolidin-2-one; at 100 ℃; for 24h; Inert atmosphere;

DOI:10.1002/chem.201606048

Reference yield: 50.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-(3’,4’-dimethoxybenzoyl)morpholine (22792-13-8) → 5,6-dimethoxyphthalide (531-88-4) + 4,5-dimethoxyisobenzofuran-1(3H)-one (4741-58-6)

Guidance literature:

With silver hexafluoroantimonate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In dichloromethane; at 160 ℃; for 72h; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1002/ejoc.202001160

upstream raw materials:

3,4-dimethoxyphthalic anhydride

formaldehyd

N-phenyl-3,4-dimethoxybenzamide

carbon monoxide

Downstream raw materials:

3,4-dimethoxy-6-nitro-phthalic acid

3,4-dimethoxy-phthalic acid

Refernces

• 1、 Hattori, Tomohiro,Ueda, Shun,Takakura, Ryoya,Sawama, Yoshinari,Monguchi, Yasunari,Sajiki, Hironao. "Heterogeneous One-Pot Carbonylation and Mizoroki–Heck Reaction in a Parallel Manner Following the Cleavage of Cinnamaldehyde Derivatives". . p. 8196 - 8202. Retrieved 2017/06/23.
• 2、 Sargent, Melvyn V.. "Naturally Occuring Dibenzofurans. Part 9. A Convenient Synthesis of Phthalides: The Synthesis of Methyl Di-O-methylporphyrilate". . p. 231 - 236. Retrieved 2007/10/02.