6,6-Dimethylcyclohex-1-ene-1-carbaldehyde

Base Information

• Chemical Name: 6,6-Dimethylcyclohex-1-ene-1-carbaldehyde
• CAS No.: 115463-65-5
• Molecular Formula: C9H14O
• Molecular Weight: 138.21
• DSSTox Substance ID: DTXSID00553869
• Mol file: 115463-65-5.mol

Synonyms:115463-65-5;6,6-Dimethylcyclohex-1-ene-1-carbaldehyde;SCHEMBL14993156;DTXSID00553869;WGKMOCKIIICBCR-UHFFFAOYSA-N;6,6-dimethylcyclohex-1-enecarbaldehyde

Chemical Property of 6,6-Dimethylcyclohex-1-ene-1-carbaldehyde

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 138.104465066
• Heavy Atom Count: 10
• Complexity: 166

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC=C1C=O)C

Technology Process of 6,6-Dimethylcyclohex-1-ene-1-carbaldehyde

There total 12 articles about 6,6-Dimethylcyclohex-1-ene-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: 49.0%

(6,6-dimethyl-1-cyclohexen-1-yl)methanol (99440-28-5) → 6,6-dimethyl-1-cyclohexenecarboxaldehyde (115463-65-5)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 1h;

Reference yield:

methyl 7-methyl-3-oxooct-6-enoate (53067-23-5) → 6,6-dimethyl-1-cyclohexenecarboxaldehyde (115463-65-5)

Guidance literature:

Multi-step reaction with 5 steps

1: stannic chloride / CH₂Cl₂ / Ambient temperature

2: 100 percent / sodium borohydride / ethanol; H₂O / 4 h / Ambient temperature

3: 58 percent / POCl₃ / pyridine / 22 h / 95 °C

4: 0.53 g / LiAlH₄ / diethyl ether / from -40 to 0 degC over 1 h

5: MnO₂ / hexane / 16 h / Ambient temperature

With manganese(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; tin(IV) chloride; trichlorophosphate; In pyridine; diethyl ether; ethanol; hexane; dichloromethane; water;

DOI:10.1002/recl.19881070304

Reference yield:

6-Methyl-hept-5-en-2-on (110-93-0,129085-68-3) → 6,6-dimethyl-1-cyclohexenecarboxaldehyde (115463-65-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 83 percent / sodium hydride / diethyl ether / 5 h reflux, overnight at room t.

2: stannic chloride / CH₂Cl₂ / Ambient temperature

3: 100 percent / sodium borohydride / ethanol; H₂O / 4 h / Ambient temperature

4: 58 percent / POCl₃ / pyridine / 22 h / 95 °C

5: 0.53 g / LiAlH₄ / diethyl ether / from -40 to 0 degC over 1 h

6: MnO₂ / hexane / 16 h / Ambient temperature

With manganese(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; tin(IV) chloride; sodium hydride; trichlorophosphate; In pyridine; diethyl ether; ethanol; hexane; dichloromethane; water;

DOI:10.1002/recl.19881070304

upstream raw materials:

(6,6-dimethyl-1-cyclohexen-1-yl)methanol

2,2-dimethylcyclohexanone (p-tolylsulfonyl)hydrazone

N,N-dimethyl-formamide

(6,6-dimethyl-cyclohex-2-enyl)-methanol

Downstream raw materials:

6,6-Dimethylcyclohex-1-ene-1-carboxylic acid

(6,6-dimethyl-1-cyclohexen-1-yl)methanol

2-(2-methylenecyclohexyl)acetic acid

(+/-)-methyl 2-methylene-1-cyclohexaneacetate