4-Phenylcyclohexanecarbaldehyde

Base Information

• Chemical Name: 4-Phenylcyclohexanecarbaldehyde
• CAS No.: 126781-72-4
• Molecular Formula: C₁₃H₁₆O
• Molecular Weight: 188.269
• European Community (EC) Number: 820-234-4
• DSSTox Substance ID: DTXSID40573804,DTXSID201287229
• Nikkaji Number: J1.068.967H
• Mol file: 126781-72-4.mol

Synonyms:1466-74-6;4-Phenylcyclohexanecarbaldehyde;4-Phenylcyclohexanecarboxaldehyde;4-PHENYLCYCLOHEXANE-1-CARBALDEHYDE;Cyclohexanecarboxaldehyde, 4-phenyl-;SCHEMBL5913558;SCHEMBL10386998;SCHEMBL17729975;SCHEMBL17752197;DTXSID40573804;IMLXMWDBBUJWOV-BJHJDKERSA-N;IMLXMWDBBUJWOV-UHFFFAOYSA-N;DTXSID201287229;cis-4-Phenylcyclohexanecarboxaldehyde;MFCD06410876;AKOS006292051;cis-4-phenylcyclohexane-1-carbaldehyde;AB25048;AC-13683;SY167404;CS-0446734;EN300-197547;J-008243;Z1198168797;126781-72-4

Chemical Property of 4-Phenylcyclohexanecarbaldehyde

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 188.120115130
• Heavy Atom Count: 14
• Complexity: 174

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(CCC1C=O)C2=CC=CC=C2

Technology Process of 4-Phenylcyclohexanecarbaldehyde

There total 3 articles about 4-Phenylcyclohexanecarbaldehyde 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: 61.0%

[4-(methoxymethylidene)cyclohexyl]benzene (701232-23-7) → cis-4-(phenyl)cyclohexane-1-carbaldehyde (126781-72-4) + trans-4-(phenyl)cyclohexane-1-carbaldehyde (37810-46-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jacs.7b09901

Reference yield:

1-phenyl-4-cyclohexanone (4894-75-1) + (methoxymethyl)triphenylphosphonium chloride (4009-98-7) → cis-4-(phenyl)cyclohexane-1-carbaldehyde (126781-72-4) + trans-4-(phenyl)cyclohexane-1-carbaldehyde (37810-46-1)

Guidance literature:

(methoxymethyl)triphenylphosphonium chloride; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; Inert atmosphere;

1-phenyl-4-cyclohexanone; In tetrahydrofuran; hexane; at 0 - 20 ℃; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; at 90 ℃; Overall yield = 73 %; Overall yield = 685 mg; Optical yield = 30 %de; Inert atmosphere;

DOI:10.1021/ja406028c

Reference yield:

1-phenyl-4-cyclohexanone (4894-75-1) → cis-4-(phenyl)cyclohexane-1-carbaldehyde (126781-72-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 21 h / -78 - 20 °C / Inert atmosphere

2.1: hydrogenchloride / tetrahydrofuran; water / 2 h / 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; In tetrahydrofuran; water;

DOI:10.1021/jacs.7b09901

upstream raw materials:

1-phenyl-4-cyclohexanone

(methoxymethyl)triphenylphosphonium chloride

[4-(methoxymethylidene)cyclohexyl]benzene