7-hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde

Base Information

• Chemical Name: 7-hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde
• CAS No.: 33279-69-5
• Molecular Formula: C₁₂H₁₂O₃
• Molecular Weight: 204.225
• DSSTox Substance ID: DTXSID10531855
• Nikkaji Number: J1.060.396J
• Mol file: 33279-69-5.mol

Synonyms:33279-69-5;7-hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde;DTXSID10531855;7-Hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbaldehyde

Chemical Property of 7-hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 204.078644241
• Heavy Atom Count: 15
• Complexity: 283

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C=CC2=CC(=C(C=C2O1)O)C=O)C

Technology Process of 7-hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde

There total 1 articles about 7-hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde 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: 49.0%

3,3-dimethyl acrylaldehyde (107-86-8) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 5-hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde (54287-99-9) + 2,2-dimethyl-7-hydroxy-2H-1-benzopyran-6-carboxaldehyde (33279-69-5)

Guidance literature:

With pyridine; for 0.416667h; Irradiation; microwave irradiation;

DOI:10.1246/bcsj.72.259

Reference yield: 60.0%

2,2-dimethyl-7-hydroxy-2H-1-benzopyran-6-carboxaldehyde (33279-69-5) + 1-(2’,4’-dibenzyloxy)phenyl-2-iodoethanone (1447625-45-7) → 7-[2-(2,4-bisbenzyloxy)phenyl-2-oxoethoxy]-2,2-dimethyl-2H-chromene-6-carboxaldehyde

Guidance literature:

With potassium carbonate; In acetone; Inert atmosphere; Reflux;

DOI:10.1021/acs.jnatprod.5b00607

Reference yield:

2,2-dimethyl-7-hydroxy-2H-1-benzopyran-6-carboxaldehyde (33279-69-5) → 2-(3,5-dimethoxyphenyl)-7,7-dimethyl-7H-furo[3,2-g]chromene

Guidance literature:

Multi-step reaction with 3 steps

1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C

1.2: 0.08 h / 0 °C

1.3: 0 - 20 °C

2.1: copper(l) iodide; potassium phosphate / tetrahydrofuran / 7 h / 80 °C / Sealed tube; Inert atmosphere

3.1: cesium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane / 6 h / 85 °C / Sealed tube

With potassium phosphate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; cesium fluoride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 3.1: |Suzuki Coupling;

DOI:10.1016/j.tetlet.2016.02.006

upstream raw materials:

3,3-dimethyl acrylaldehyde

2,4-Dihydroxybenzaldehyde

Downstream raw materials:

4',2-dibenzyloxy-2'-hydroxy-2,2-dimethyl-2H-pyrano<2,3-b>chalcone

7-(benzyloxy)-2,2-dimethyl-2H-1-benzopyran-6-carboxaldehyde

2-(4-hydroxyphenyl)-7,7-dimethyl-7H-furo[3,2-g]chromene

2-(4'-methoxyphenyl)-7,7-dimethyl-7H-furo[3,2-g]chromene