2-Methyl-6-oxocyclopent-1-enyl acetate

Base Information

• Chemical Name: 2-Methyl-6-oxocyclopent-1-enyl acetate
• CAS No.: 1196-22-1
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• European Community (EC) Number: 214-809-3
• NSC Number: 109960
• DSSTox Substance ID: DTXSID20152515
• Nikkaji Number: J203.468I
• Wikidata: Q63398059
• Mol file: 1196-22-1.mol

Synonyms:Cyclotene acetate;1196-22-1;2-Methyl-6-oxocyclopent-1-enyl acetate;EINECS 214-809-3;2-methyl-5-oxocyclopent-1-en-1-yl acetate;2-Cyclopenten-1-one,2-(acetyloxy)-3-methyl-;NSC109960;SCHEMBL10861612;DTXSID20152515;AKOS006303599;NSC 109960;NSC-109960;2-Acetyloxy-3-methyl-2-cyclopenten-1-one;2-ACETOXY-3-METHYL-2-CYCLOPENTEN-1-ONE;Q63398059

Chemical Property of 2-Methyl-6-oxocyclopent-1-enyl acetate

Chemical Property:

• Vapor Pressure: 0.00437mmHg at 25°C
• Refractive Index: 1.477
• Boiling Point: 278 °C at 760 mmHg
• Flash Point: 121.6 °C
• Density: 1.13 g/cm³
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 154.062994177
• Heavy Atom Count: 11
• Complexity: 238

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)CC1)OC(=O)C

Technology Process of 2-Methyl-6-oxocyclopent-1-enyl acetate

There total 5 articles about 2-Methyl-6-oxocyclopent-1-enyl acetate 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: 97.0%

2-hydroxy-3-methylcyclopent-2-en-1-one (80-71-7) + acetic anhydride (108-24-7) → 2-methyl-5-oxocyclopent-1-en-1-yl acetate (1196-22-1)

Guidance literature:

With triethylamine; In ethanol; at 20 ℃; for 1h;

DOI:10.1002/cssc.201702100

Reference yield: 75.0%

→ 2-methyl-5-oxocyclopent-1-en-1-yl acetate (1196-22-1)

Guidance literature:

Reference yield:

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → 2-methyl-5-oxocyclopent-1-en-1-yl acetate (1196-22-1)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen; [Ir(η⁵-Cp*)(2,2'-dipyridylamine)Cl]Cl / water / 2 h / 120 °C / 7500.75 Torr

2: potassium tert-butylate / tetrahydrofuran / 0.08 h / 60 °C

3: triethylamine / ethanol / 1 h / 20 °C

With [Ir(η⁵-Cp*)(2,2'-dipyridylamine)Cl]Cl; potassium tert-butylate; hydrogen; triethylamine; In tetrahydrofuran; ethanol; water; 1: |Aldol Condensation / 2: |Aldol Condensation;

DOI:10.1002/cssc.201702100

upstream raw materials:

3-methyl-1,2-cyclopentanedione

acetic anhydride

acetyl chloride

2-hydroxy-3-methylcyclopent-2-en-1-one

Downstream raw materials:

7-methyl-1,4-dioxaspiro[4.4]nonan-6-one