6-(4-Methoxyphenyl)oxane-2,4-dione

Base Information

• Chemical Name: 6-(4-Methoxyphenyl)oxane-2,4-dione
• CAS No.: 133286-42-7
• Molecular Formula: C12H12O4
• Molecular Weight: 220.225
• ChEMBL ID: CHEMBL365708
• DSSTox Substance ID: DTXSID30568401
• Mol file: 133286-42-7.mol

Synonyms:6-(4-Methoxyphenyl)oxane-2,4-dione;133286-42-7;CHEMBL365708;DTXSID30568401;6-(4-methoxyphenyl)-tetrahydropyrane-2,4-dione

Chemical Property of 6-(4-Methoxyphenyl)oxane-2,4-dione

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 220.07355886
• Heavy Atom Count: 16
• Complexity: 279

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2CC(=O)CC(=O)O2

Technology Process of 6-(4-Methoxyphenyl)oxane-2,4-dione

There total 4 articles about 6-(4-Methoxyphenyl)oxane-2,4-dione 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: 74.0%

ethyl acetoacetate (141-97-9) + 4-methoxy-benzaldehyde (123-11-5) → 6-(4-methoxyphenyl)dihydro-2H-pyran-2,4(3H)-dione (133286-42-7)

Guidance literature:

ethyl acetoacetate; 4-methoxy-benzaldehyde; With potassium carbonate; In ethanol; at 45 ℃; for 18h;

With hydrogenchloride; In ethanol; water; at 20 ℃; pH=1;

DOI:10.1246/bcsj.20130069

Reference yield:

4-methoxy-benzaldehyde (123-11-5) + acetoacetic acid methyl ester (105-45-3) → 6-(4-methoxyphenyl)dihydro-2H-pyran-2,4(3H)-dione (133286-42-7)

Guidance literature:

acetoacetic acid methyl ester; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.333333h;

4-methoxy-benzaldehyde; In tetrahydrofuran; for 0.5h;

With potassium hydroxide; for 5h;

DOI:10.1023/A:1011913328785

Reference yield:

ethyl acetoacetate (141-97-9) + 4-methoxy-benzaldehyde (123-11-5) → 6-(4-methoxyphenyl)dihydro-2H-pyran-2,4(3H)-dione (133286-42-7) + ethyl 5-hydroxy-5-(4-methoxyphenyl)-3-oxopentanoate (682770-51-0)

Guidance literature:

ethyl acetoacetate; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.333333h;

4-methoxy-benzaldehyde; In tetrahydrofuran; for 0.5h; Title compound not separated from byproducts;

DOI:10.1023/A:1011913328785

upstream raw materials:

ethyl acetoacetate

4-methoxy-benzaldehyde

acetoacetic acid methyl ester

Downstream raw materials:

trifluoromethanesulfonic acid 2-(4-methoxyphenyl)-6-oxo-3,6-dihydro-2H-pyran-4-yl ester

(E)-2-[1,3]Dithiolan-2-ylidene-5-(4-methoxy-phenyl)-3-oxo-pent-4-enoic acid

(E)-1-[1,3]Dithiolan-2-ylidene-4-(4-methoxy-phenyl)-but-3-en-2-one

Refernces

• 1、 Hossain, Md. Imran,Shaban, Elkhabiry,Ikemi, Taku,Peng, Wei,Kawafuchi, Hiroyuki,Inokuchi, Tsutomu. "Annulation of 2H-pyran onto 1-Oxa- or 1-azacyclohexane-2,4-diones and their analogues via sequential condensation with -substituted enals and 6π-electrocyclization". supporting information. p. 870 - 879. Retrieved 2013/08/15.
• 2、 Lokot',Pashkovskii,Lakhvich. "Synthesis of 3- and 5-alkyl-6-alkyl(aryl)tetrahydropyran-2,4-diones by the condensation of β-oxo acid esters with aldehydes and ketones". . p. 707 - 714. Retrieved 2007/10/03.