2,6,6-Trimethyl-5-oxocyclohexa-1,3-diene-1-carbaldehyde

Base Information

• Chemical Name: 2,6,6-Trimethyl-5-oxocyclohexa-1,3-diene-1-carbaldehyde
• CAS No.: 141891-13-6
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.204
• DSSTox Substance ID: DTXSID70577279
• Wikidata: Q82467235
• Mol file: 141891-13-6.mol

Synonyms:141891-13-6;2,6,6-Trimethyl-5-oxocyclohexa-1,3-diene-1-carbaldehyde;DTXSID70577279

Chemical Property of 2,6,6-Trimethyl-5-oxocyclohexa-1,3-diene-1-carbaldehyde

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 293

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(C(=O)C=C1)(C)C)C=O

Technology Process of 2,6,6-Trimethyl-5-oxocyclohexa-1,3-diene-1-carbaldehyde

There total 7 articles about 2,6,6-Trimethyl-5-oxocyclohexa-1,3-diene-1-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: 12.1%

2-hydroxymethyl-1,1,3-trimethyl-3,5-cyclohexadiene (73527-23-8) → 3-keto-2,2,6-trimethylcyclohexa-4,6-dienocarboxaldehyde (141891-13-6)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1248/cpb.29.105

Reference yield:

3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3,8022-83-1) → 3-keto-2,2,6-trimethylcyclohexa-4,6-dienocarboxaldehyde (141891-13-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 25 percent / NaOAc / acetic acid / 0.25 h / Ambient temperature

2: 65 percent / trifluoroacetic acid / CH₂Cl₂ / 0.25 h / 0 °C

3: 46.2 percent / 30percent H₂O₂ / methanol / 0.17 h / 0 °C

4: 93 percent / CCl₄ / 16 h / Heating

5: 88.5 percent / thionyl chloride, pyridine / CH₂Cl₂ / 0.08 h / 0 °C

6: 90.6 percent / 1N KOH / methanol / 4 h / Ambient temperature

7: 12.1 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; potassium hydroxide; thionyl chloride; dihydrogen peroxide; sodium acetate; pyridinium chlorochromate; trifluoroacetic acid; In methanol; tetrachloromethane; dichloromethane; acetic acid;

DOI:10.1248/cpb.29.105

Reference yield:

(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate (37715-31-4) → 3-keto-2,2,6-trimethylcyclohexa-4,6-dienocarboxaldehyde (141891-13-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaBH₄ / 1.) ethanol, r.t., 15 min; 2.) ethanol, r.t., 1.5 h

2: 65 percent / trifluoroacetic acid / CH₂Cl₂ / 0.25 h / 0 °C

3: 46.2 percent / 30percent H₂O₂ / methanol / 0.17 h / 0 °C

4: 93 percent / CCl₄ / 16 h / Heating

5: 88.5 percent / thionyl chloride, pyridine / CH₂Cl₂ / 0.08 h / 0 °C

6: 90.6 percent / 1N KOH / methanol / 4 h / Ambient temperature

7: 12.1 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; potassium hydroxide; sodium tetrahydroborate; thionyl chloride; dihydrogen peroxide; pyridinium chlorochromate; trifluoroacetic acid; In methanol; tetrachloromethane; dichloromethane;

DOI:10.1248/cpb.29.105

upstream raw materials:

2-hydroxymethyl-1,1,3-trimethyl-3,5-cyclohexadiene

(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate

3,7-dimethyl-2E,6-octadien-1-yl acetate

2-acetoxymethyl-3-hydroxy-1,1,3-trimethyl-6-phenylselenylcyclohexane