2H-1-Benzopyran-5-carboxaldehyde, 6-hydroxy-7-methoxy-2-oxo-

Base Information

• Chemical Name: 2H-1-Benzopyran-5-carboxaldehyde, 6-hydroxy-7-methoxy-2-oxo-
• CAS No.: 68468-11-1
• Molecular Formula: C11H8O5
• Molecular Weight: 220.18
• DSSTox Substance ID: DTXSID70218579
• Wikidata: Q83095453
• Mol file: 68468-11-1.mol

Synonyms:68468-11-1;5-Formyl-6-hydroxy-7-methoxycoumarin;2H-1-Benzopyran-5-carboxaldehyde, 6-hydroxy-7-methoxy-2-oxo-;6-Hydroxy-7-methoxy-2-oxo-2H-chromene-5-carbaldehyde;DTXSID70218579

Chemical Property of 2H-1-Benzopyran-5-carboxaldehyde, 6-hydroxy-7-methoxy-2-oxo-

Chemical Property:

• Vapor Pressure: 3.07E-08mmHg at 25°C
• Boiling Point: 436.8°C at 760 mmHg
• Flash Point: 177.8°C
• PSA: 76.74000
• Density: 1.456g/cm³
• LogP: 1.31970
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 220.03717335
• Heavy Atom Count: 16
• Complexity: 324

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=C2C=CC(=O)OC2=C1)C=O)O

Technology Process of 2H-1-Benzopyran-5-carboxaldehyde, 6-hydroxy-7-methoxy-2-oxo-

There total 12 articles about 2H-1-Benzopyran-5-carboxaldehyde, 6-hydroxy-7-methoxy-2-oxo- 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:

4-isopropyloxy-3-methoxybenzaldehyde (2538-98-9) → 5-Formyl-6-hydroxy-7-methoxycoumarin (68468-11-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 73.6 percent / HCOOH, 30percent aq. H₂O₂ / 3.5 h / 0 - 5 °C

2: 95.5 percent / K₂CO₃ / dimethylformamide / 12.5 h / 60 - 70 °C

3: 96.6 percent / POCl₃ / CH₂Cl₂ / 6 h / Ambient temperature

4: 92.7 percent / H₂ / 5percent Pd/C / methanol / 760 Torr / Ambient temperature

5: 45.7 percent / AcONa / 120 h / Heating

6: 96.5 percent / H₂SO₄ / acetic acid / 2.5 h / Heating

7: 96.8 percent / K₂CO₃ / acetone / 7 h / Heating

8: 57.6 percent / CsF / various solvent(s) / 3 h / 190 - 195 °C / Heating

9: 1.) (CF₃CO)2O, 30percent aq. H₂O₂, 2.) NaIO₄, 3.) 1percent aq NaHCO₃

With sodium periodate; formic acid; sulfuric acid; hydrogen; dihydrogen peroxide; sodium acetate; sodium hydrogencarbonate; potassium carbonate; cesium fluoride; trifluoroacetic anhydride; trichlorophosphate; palladium on activated charcoal; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.40.2614

Reference yield:

vanillin (121-33-5,8014-42-4) → 5-Formyl-6-hydroxy-7-methoxycoumarin (68468-11-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 94.6 percent / K₂CO₃ / dimethylformamide / 6 h / 60 - 65 °C

2: 73.6 percent / HCOOH, 30percent aq. H₂O₂ / 3.5 h / 0 - 5 °C

3: 95.5 percent / K₂CO₃ / dimethylformamide / 12.5 h / 60 - 70 °C

4: 96.6 percent / POCl₃ / CH₂Cl₂ / 6 h / Ambient temperature

5: 92.7 percent / H₂ / 5percent Pd/C / methanol / 760 Torr / Ambient temperature

6: 45.7 percent / AcONa / 120 h / Heating

7: 96.5 percent / H₂SO₄ / acetic acid / 2.5 h / Heating

8: 96.8 percent / K₂CO₃ / acetone / 7 h / Heating

9: 57.6 percent / CsF / various solvent(s) / 3 h / 190 - 195 °C / Heating

10: 1.) (CF₃CO)2O, 30percent aq. H₂O₂, 2.) NaIO₄, 3.) 1percent aq NaHCO₃

With sodium periodate; formic acid; sulfuric acid; hydrogen; dihydrogen peroxide; sodium acetate; sodium hydrogencarbonate; potassium carbonate; cesium fluoride; trifluoroacetic anhydride; trichlorophosphate; palladium on activated charcoal; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.40.2614

Reference yield:

4-isopropoxy-3-methoxyphenol (86636-03-5) → 5-Formyl-6-hydroxy-7-methoxycoumarin (68468-11-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 95.5 percent / K₂CO₃ / dimethylformamide / 12.5 h / 60 - 70 °C

2: 96.6 percent / POCl₃ / CH₂Cl₂ / 6 h / Ambient temperature

3: 92.7 percent / H₂ / 5percent Pd/C / methanol / 760 Torr / Ambient temperature

4: 45.7 percent / AcONa / 120 h / Heating

5: 96.5 percent / H₂SO₄ / acetic acid / 2.5 h / Heating

6: 96.8 percent / K₂CO₃ / acetone / 7 h / Heating

7: 57.6 percent / CsF / various solvent(s) / 3 h / 190 - 195 °C / Heating

8: 1.) (CF₃CO)2O, 30percent aq. H₂O₂, 2.) NaIO₄, 3.) 1percent aq NaHCO₃

With sodium periodate; sulfuric acid; hydrogen; dihydrogen peroxide; sodium acetate; sodium hydrogencarbonate; potassium carbonate; cesium fluoride; trifluoroacetic anhydride; trichlorophosphate; palladium on activated charcoal; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.40.2614

upstream raw materials:

4-methoxy-2-methyl-7H-furo<3,2-f><1>-benzopyran-7-one

isoscopoletin

4-isopropyloxy-3-methoxybenzaldehyde

vanillin

Refernces

• 1、 Ishii,Ishikawa,Wada,Miyazaki,Kaneko,Harayama. "Synthetic studies on naturally occurring coumarins. II. Synthesis of 6,7-dimethoxy- and 7,8-dimethoxy-5-[(E)-3-oxo-1-butenyl]coumarins". . p. 2614 - 2619. Retrieved 2007/10/02.