Cyclopropanecarboxaldehyde, 2-(4-methylphenyl)-, cis- (9CI)

Base Information

• Chemical Name: Cyclopropanecarboxaldehyde, 2-(4-methylphenyl)-, cis- (9CI)
• CAS No.: 153198-69-7
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160.216
• Mol file: 153198-69-7.mol

Synonyms:Cyclopropanecarboxaldehyde, 2-(4-methylphenyl)-, cis- (9CI)

Chemical Property of Cyclopropanecarboxaldehyde, 2-(4-methylphenyl)-, cis- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclopropanecarboxaldehyde, 2-(4-methylphenyl)-, cis- (9CI)

There total 25 articles about Cyclopropanecarboxaldehyde, 2-(4-methylphenyl)-, cis- (9CI) 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: 79.0%

(2-p-Tolyl-cyclopropyl)-methanol (114095-61-3) → 2-(p-tolyl)cyclopropanecarbaldehyde (132145-62-1,153198-69-7)

Guidance literature:

With 2,2'-bipyridine-chromium(VI) oxide; In dichloromethane; at 0 - 5 ℃;

DOI:10.1002/mrc.1260281110

Reference yield:

ethyl (E)-3-(4-methylphenyl)acrylate (97585-04-1,20511-20-0,24393-49-5) → trans-2-(p-tolyl)cyclopropane-1-carbaldehyde (132145-62-1,153198-69-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / dimethyl sulfoxide / 1 h / Inert atmosphere

1.2: 108 h / 0 - 65 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / diethyl ether / 6 h / Inert atmosphere; Reflux

3.1: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; sodium hydride; pyridinium chlorochromate; In diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/acs.orglett.8b02094

Reference yield:

(trans-2-(4-methylphenyl)cyclopropyl)methanol (114095-61-3) → trans-2-(p-tolyl)cyclopropane-1-carbaldehyde (132145-62-1,153198-69-7)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b02094

upstream raw materials:

(2-p-Tolyl-cyclopropyl)-methanol

ethyl 2-(4-methylphenyl)cyclopropane-1-carboxylate

4-methylcinnamyl alcohol

C₁₂H₁₅NO₂

Refernces

• 1、 Banerjee, Prabal,Dey, Raghunath,Rajput, Shruti. "Metal-free domino Cloke-Wilson rearrangement-hydration-dimerization of cyclopropane carbaldehydes: A facile access to oxybis(2-aryltetrahydrofuran) derivatives". . . Retrieved 2020/03/13.
• 2、 Banerjee, Prabal,Kumar, Pankaj,Kumar, Rakesh. "Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine". . p. 6535 - 6550. Retrieved 2020/06/09.