3-Methoxyphthalide

Base Information

• Chemical Name: 3-Methoxyphthalide
• CAS No.: 4122-57-0
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• Hs Code.: 2932209090
• European Community (EC) Number: 677-566-6
• NSC Number: 408564
• DSSTox Substance ID: DTXSID70875863
• Nikkaji Number: J343.988G
• Mol file: 4122-57-0.mol

Synonyms:4122-57-0;3-Methoxyphthalide;3-Methoxy-1(3H)-isobenzofuranone;3-Methoxyisobenzofuran-1(3H)-one;3-methoxy-3H-2-benzofuran-1-one;3-Methoxy-2-benzofuran-1(3H)-one;NSC408564;MFCD01652196;NSC 408564;3-methoxy-1,3-dihydro-2-benzofuran-1-one;SCHEMBL2631833;DTXSID70875863;3-methoxy-3H-isobenzofuran-1-one;AC7707;3-Methoxyisobenzo[b]furan-1(3H)-one;AKOS004907326;3-Methoxy-2-isobenzofuran-1(3H)-one;NSC-408564;AS-60992;SY017409;1(3H)-ISOBENZOFURANONE-3-METHOXYL;CS-0186840;FT-0755131;M2007;A847582;AI-942/25034663

Chemical Property of 3-Methoxyphthalide

Chemical Property:

• Vapor Pressure: 0.00157mmHg at 25°C
• Melting Point: 45oC
• Boiling Point: 295°Cat760mmHg
• Flash Point: 119.5°C
• PSA: 35.53000
• Density: 1.25g/cm³
• LogP: 1.50200
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 164.047344113
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Methoxyisobenzofuran-1(3H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1C2=CC=CC=C2C(=O)O1
• Uses: 3-Methoxyisobenzofuran-1(3H)-one acts as a reagent for the synthesis of vitamin K and related naphthoquinones via demethoxycarbonylative cyclization and cascade Cope-retro-Wittig rearrangement.

Technology Process of 3-Methoxyphthalide

There total 14 articles about 3-Methoxyphthalide 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: 67.0%

naphthalene (91-20-3,71998-51-1,72931-45-4) → 3-methoxy-1,3-dihydro-2-benzofuran-1-ol + 3-hydroxy-1,3-dihydro-2-benzofuran-1-yl acetate + 3-methoxy-3H-isobenzofuran-1-one (4122-57-0) + methyl o-formylbenzoate (4122-56-9)

Guidance literature:

naphthalene; With oxygen; ozone; In methanol;

With acetic acid; potassium iodide; In methanol; for 1.5h;

DOI:10.1134/S1070428006030109

Reference yield: 59.0%

naphthalene (91-20-3,71998-51-1,72931-45-4) → 3-methoxy-3H-isobenzofuran-1-one (4122-57-0) + methyl o-formylbenzoate (4122-56-9)

Guidance literature:

naphthalene; With oxygen; ozone; In methanol;

With acetic acid; potassium iodide; In methanol;

DOI:10.1134/S1070428006030109

Reference yield: 50.0%

methyl o-formylbenzoate (4122-56-9) + diethylzinc (557-20-0) → 3-methoxy-3H-isobenzofuran-1-one (4122-57-0) + 3-ethoxy-3H-isobenzofuran-1-one (16824-02-5)

Guidance literature:

With 1,1-diethyl-3-(3'-indolyl)-(2S)-(N-methyl-N-3'',3''-dimethylbutylamino)-1-propanol; In hexane; toluene; at -15 ℃; Inert atmosphere;

DOI:10.1002/ejoc.200900422

upstream raw materials:

methanol

3-chloro-1(3H)-isobenzofuranone

2-methyl-1-indanone hydrazone

N,N-bis<1'(3'H)-isobenzofuranon-3'-yl>-4-aminobutyric acid

Downstream raw materials:

o-phthalic dicarboxaldehyde

phthalyl alcohol

menadione

1,3-di(4-(4,4-dimethyloxazolidin-2-yl)phenyl)isobenzofuran

Refernces

• 1、 Ren, Jie,Jiang, Ju-Xing,Li, Ang-Bo,Liao, Tou-Geng,Tian, Ren-Rong,Chen, Xu-Lin,Jiang, Si-Ping,Pittman Jr., Charles U.,Zhu, Hua-Jie. "Assignment of the absolute configuration of concentricolide - absolute configuration determination of its bioactive analogs using DFT methods". supporting information; experimental part. p. 3987 - 3991. Retrieved 2010/02/27.
• 2、 Morgan, David O.,David Ollis,Stanforth, Stephen P.. "Preparation and cycloaddition reactions of novel heterocyclic mesomeric betaines". . p. 5523 - 5534. Retrieved 2007/10/03.