1H-2-Benzopyran-1-one, 3,4-dihydro-3-(4-methylphenyl)-

Base Information

• Chemical Name: 1H-2-Benzopyran-1-one, 3,4-dihydro-3-(4-methylphenyl)-
• CAS No.: 95217-41-7
• Molecular Formula: C16H14O2
• Molecular Weight: 238.286
• DSSTox Substance ID: DTXSID70453084
• Nikkaji Number: J515.085J
• Mol file: 95217-41-7.mol

Synonyms:1H-2-Benzopyran-1-one, 3,4-dihydro-3-(4-methylphenyl)-;95217-41-7;3-(4-methylphenyl)isochroman-1-one;DTXSID70453084

Chemical Property of 1H-2-Benzopyran-1-one, 3,4-dihydro-3-(4-methylphenyl)-

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 238.099379685
• Heavy Atom Count: 18
• Complexity: 304

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C2CC3=CC=CC=C3C(=O)O2

Technology Process of 1H-2-Benzopyran-1-one, 3,4-dihydro-3-(4-methylphenyl)-

There total 10 articles about 1H-2-Benzopyran-1-one, 3,4-dihydro-3-(4-methylphenyl)- 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: 76.0%

1-ethenyl-4-methylbenzene (622-97-9,24936-41-2) + ortho-carboxybenzenediazonium tetrafluoroborate (14783-89-2) → 3-(4-methylphenyl)-3,4-dihydro-1H-isochromen-1-one (95217-41-7)

Guidance literature:

With {Ru(dipy)3}Cl₂*nH₂O; In acetonitrile; at 23 ℃; for 2h; Sealed tube; Irradiation; Inert atmosphere;

DOI:10.1002/ejoc.201601458

Reference yield: 60.0%

4-methyl-benzaldehyde (104-87-0) + 2-ethoxycarbonylbenzyl bromide (7115-91-5) → 3-(4-methylphenyl)-3,4-dihydro-1H-isochromen-1-one (95217-41-7)

Guidance literature:

With bis(cyclopentadienyl)titanium dichloride; zinc; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetlet.2007.03.172

Reference yield:

ortho-methylbenzoic acid (118-90-1) → 3-(4-methylphenyl)-3,4-dihydro-1H-isochromen-1-one (95217-41-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / thionyl chloride / 18 h / Ambient temperature

2: 100 percent / CH₂Cl₂ / 0.5 h / 0 °C

3: 92 percent / thionyl chloride / 1 h

4: 1.) n-BuLi / 1.) ethyl ether, 0 deg C, 1 h, 2.) RT, overnight

With n-butyllithium; thionyl chloride; In dichloromethane;

DOI:10.1021/jo00208a020

upstream raw materials:

4-methyl-benzaldehyde

4,5-dihydro-4,4-dimethyl-2-(2-methylphenyl)-2-oxazoline

1-tert-Butyl-3-(p-tolyl)-3,4-dihydro-1H-2-benzopyran-1-ol

2-ethoxycarbonylbenzyl bromide