1(3H)-Isobenzofuranone, 3-hydroxy-5,7-dimethoxy-

Base Information

• Chemical Name: 1(3H)-Isobenzofuranone, 3-hydroxy-5,7-dimethoxy-
• CAS No.: 85925-67-3
• Molecular Formula: C10H10O5
• Molecular Weight: 210.186
• DSSTox Substance ID: DTXSID50372906
• Nikkaji Number: J2.517.355D
• Mol file: 85925-67-3.mol

Synonyms:85925-67-3;1(3H)-Isobenzofuranone, 3-hydroxy-5,7-dimethoxy-;DTXSID50372906;AKOS004907427;3-hydroxy-5,7-dimethoxy-3H-isobenzofuran-1-one;3-Hydroxy-5,7-dimethoxyisobenzofuran-1(3H)-one;3-hydroxy-5,7-dimethoxy-2-benzofuran-1(3H)-one

Chemical Property of 1(3H)-Isobenzofuranone, 3-hydroxy-5,7-dimethoxy-

Chemical Property:

• PSA: 64.99000
• LogP: 0.86510
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 210.05282342
• Heavy Atom Count: 15
• Complexity: 254

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C(=C1)OC)C(=O)OC2O

Technology Process of 1(3H)-Isobenzofuranone, 3-hydroxy-5,7-dimethoxy-

There total 4 articles about 1(3H)-Isobenzofuranone, 3-hydroxy-5,7-dimethoxy- 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:

N,N-diethyl 2-formyl-4,6-dimethoxybenzamide (868756-10-9) → 2-formyl-4,6-dimethoxy-benzoic acid (17846-89-8) + 3-hydroxy-5,7-dimethoxy-(3H)-isobenzofuran-1-one (85925-67-3)

Guidance literature:

With hydrogenchloride; water; acetic acid; for 12h; Overall yield = 96 %; Reflux;

DOI:10.1016/j.bmcl.2013.01.074

Reference yield:

N,N-diethyl-2,4-dimethoxybenzamide (142601-55-6) → 2-formyl-4,6-dimethoxy-benzoic acid (17846-89-8) + 3-hydroxy-5,7-dimethoxy-(3H)-isobenzofuran-1-one (85925-67-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sec.-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; cyclohexane / 2 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: hydrogenchloride; acetic acid; water / 12 h / Reflux

With hydrogenchloride; N,N,N,N,-tetramethylethylenediamine; water; sec.-butyllithium; acetic acid; In tetrahydrofuran; cyclohexane;

DOI:10.1016/j.bmcl.2013.01.074

Reference yield:

2,4 dimethoxybenzoic acid (91-52-1) → 2-formyl-4,6-dimethoxy-benzoic acid (17846-89-8) + 3-hydroxy-5,7-dimethoxy-(3H)-isobenzofuran-1-one (85925-67-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: thionyl chloride / 3 h / Inert atmosphere; Reflux

2.1: dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

3.1: sec.-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; cyclohexane / 2 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: hydrogenchloride; acetic acid; water / 12 h / Reflux

With hydrogenchloride; thionyl chloride; N,N,N,N,-tetramethylethylenediamine; water; sec.-butyllithium; acetic acid; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1016/j.bmcl.2013.01.074

upstream raw materials:

N,N-diethyl-2,4-dimethoxybenzamide

N,N-diethyl 2-formyl-4,6-dimethoxybenzamide

2,4 dimethoxybenzoic acid

2,4-dimethoxybenzoyl chloride

Downstream raw materials:

methyl 2-formyl-4,6-dimethoxybenzoate

Methyl 2-carboxy-3,5-dimethoxy-(E)-cinnamate