1-Acetyl-4-methyl-1,3-cyclohexadiene

Base Information

• Chemical Name: 1-Acetyl-4-methyl-1,3-cyclohexadiene
• CAS No.: 24243-12-7
• Molecular Formula: C9H12O
• Molecular Weight: 136.19100
• Mol file: 24243-12-7.mol

Synonyms:1-Acetyl-4-methyl-cyclohexadien-1,3;1-(4-Methyl-cyclohexa-1,3-dienyl)-ethanone;1-Acetyl-4-methyl-1,3-cyclohexadiene;4-Methyl-cyclohexa-1,3-dien-1-yl-methyl-keton;

Chemical Property of 1-Acetyl-4-methyl-1,3-cyclohexadiene

Chemical Property:

• Boiling Point: 92 °C (10 mmHg)
• PSA: 17.07000
• LogP: 2.24190

Purity/Quality:

1-Acetyl-4-methyl-1,3-cyclohexadiene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Acetyl-4-methyl-1,3-cyclohexadiene

There total 9 articles about 1-Acetyl-4-methyl-1,3-cyclohexadiene 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: 65.0%

1-[2-(2-Methoxy-ethoxy)-4-methyl-cyclohex-3-enyl]-ethanone (91228-24-9,91228-25-0) → 1-(4-methyl-1,3-cyclohe4xadienyl)-1-ethanone (24243-12-7)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1021/jo00193a028

Reference yield:

6-(2',2',3'-trimethylcyclobutyl)3,5-heptadiene-2-one → 1-(4-methyl-1,3-cyclohe4xadienyl)-1-ethanone (24243-12-7) + (+)-(2S:6S)-trans-α-irone (90242-81-2,54082-69-8) + (E,2S,6R)-(-)-cis-α-irone (89888-03-9,54082-69-8)

Guidance literature:

In pentane; at 310 ℃; under 760 Torr;

DOI:10.1002/hlca.19840670139

Reference yield:

1-(β-methoxyethoxy)-3-methyl-1,3-butadiene (91237-76-2,91237-77-3) → 1-(4-methyl-1,3-cyclohe4xadienyl)-1-ethanone (24243-12-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / hydroquinone / benzene / 24 h / Ambient temperature

2: 27 percent / NaOCH₃ / methanol / 1 h / Ambient temperature

With sodium methylate; hydroquinone; In methanol; benzene;

DOI:10.1021/jo00193a028

upstream raw materials:

CH₃C₆H₄CH(CH₃)OH

methyl vinyl ketone

1-acetyl-4-methyl-3-cyclohexen-1-ol

Carbonic acid ethyl ester (E)-3-methyl-buta-1,3-dienyl ester

Refernces

• 1、 Rautenstrauch, Valentin,Willhalm, Bruno,Thommen, Walter,Ohloff, Guenther. "38. On The Stereochemistry of the Irones". . p. 325 - 331. Retrieved 1984.
• 2、 De Cusati, Paul F.,Olofson. "O-1-(1,3-butadienyl) carbamates as diels-alder dienes: Stereospecific synthesis of (±)-Hernandulcin and congeners". . p. 1409 - 1412. Retrieved 2007/10/02.