ChemicalBook CAS DataBase List 2-chlorocumene

2-chlorocumene synthesis

11synthesis methods

Product Name:2-chlorocumene
CAS Number:2077-13-6
Molecular formula:C9H11Cl
Molecular Weight:154.6366

98-82-8
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Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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934-53-2 Synthesis

934-53-2
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$45.00/50mg

2077-13-6
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2621-46-7
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3360-52-9
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103-89-9
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$6.00/5g

Yield: 86% ， 70% ， 20%

Reaction Conditions:

at 110; for 12 h;Mechanism;Darkness;Orton Haloaniline Rearrangement;

Steps:

Thermal rearrangement ofN-chloro-N-(4-methylphenyl)acetamide in cumene
N-Chloro-N-(4-methylphenyl)acetamide (366 mg, 2 mmol)was dissolved in cumene (5 mL) in a round-bottom ask.After covered the ask with aluminum foil, the solutionwas heated at 110°C under stirring for 12 h. The reactionmixture was monitored by TLC and GC-MS. Evaporationof the solvent and purifcation by silica gel column chromatography aorded products N-(4-methylphenyl)acetamide256 mg (86% yield), 4-chlorocumene 215 mg (70% yield) and(1-chloromethyl)vinylbenzene 61 mg (20% yield). In addition, GC analysis of the crude reaction mixture indicatedthat N-(2-chloro-4-methylphenyl)acetamide, 4-chlorocumene,and 2-chlorocumene generated in 5%, 4.5%, and 0.5% yields,respectively.

References:

Cheng, Baoxiang;Xu, Jiaxi [Phosphorus, Sulfur and Silicon and the Related Elements,2017,vol. 192,# 5,p. 518 - 525]

110-05-4 Synthesis