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ChemicalBook--->CAS DataBase List--->3274-12-2

3274-12-2

3274-12-2 Structure

3274-12-2 Structure
IdentificationBack Directory
[Name]

4-METHYL-4-TRICHLOROMETHYL-2,5-CYCLOHEXADIEN-1-ONE)
[CAS]

3274-12-2
[Synonyms]

NSC 407523
4-Methyl-4-(trichloromethyl)cyclohexa-2,5-dienone
4-Trichloromethyl-4-methyl-2,5-cyclohexadien-1-one
4-Methyl-4-(trichloroMeth yl)-2,5-cyclohexadienone
4-METHYL-4-TRICHLOROMETHYL-2,5-CYCLOHEXADIEN-1-ONE)
4-Methyl-4-(trichloroMethyl)cyclohexa-2,5-dien-1-one
2,5-Cyclohexadien-1-one,4-Methyl-4-(trichloroMethyl)-
4-Methyl-4-(trichloromethyl)-2,5-cyclohexadiene-1-one
4-Methyl-4-(trichloromethyl)-2,5-cyclohexadienone (4-MTD)
[Molecular Formula]

C8H7Cl3O
[MDL Number]

MFCD00001590
[MOL File]

3274-12-2.mol
[Molecular Weight]

225.5
Chemical PropertiesBack Directory
[Melting point ]

103-104℃ (ligroine )
[Boiling point ]

289.0±40.0 °C(Predicted)
[density ]

1.419±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,2-8°C
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P280-P305+P351+P338
Hazard InformationBack Directory
[Synthesis]

Carbon tetrachloride

56-23-5

p-Cresol

106-44-5

4-METHYL-4-TRICHLOROMETHYL-2,5-CYCLOHEXADIEN-1-ONE)

3274-12-2

In this embodiment, 4-methyl-4-(trichloromethyl)cyclohexa-2,5-dienone is prepared, comprising the following steps: S1: 160 g of aluminum trichloride was weighed and added to 670 g of dichloroethane, placed in a reaction flask with stirring, and cooled to 5 °C. Weigh 100g of p-toluol dissolved in 330g of dichloroethane, placed in a constant pressure dropping funnel, and slowly added dropwise to the dichloroethane reaction system of aluminum trichloride. The reaction temperature was maintained at 11°C during the dropwise addition. After the dropwise addition was completed, 140 g of carbon tetrachloride was added, the temperature was raised to 38°C, and the reaction was continued with stirring for 2 hours. Upon completion of the reaction, the heating was stopped. In this step, p-toluene and carbon tetrachloride were used as the reaction feedstock, aluminum trichloride was used as the catalyst, and dichloroethane was used as the solvent. S2: The reaction mixture was cooled to room temperature and then slowly added to 1000 g of ice water and stirred for 30 min. S3: Liquid-liquid separation was carried out at 5°C, and vacuum distillation was used to remove the organic solvent to obtain 195 g of residue. S4: 488 g of methanol and 10 g of activated carbon were added to the residue, heated to reflux (78°C) and stirred for 30 minutes. After hot filtration, the precipitated solid was cooled, filtered and dried to give 184g of wet crystalline product, which showed higher purity by HPLC. S5: 184 g of crude product was mixed with 460 g of methanol, 9.2 g of activated charcoal was added and heated to reflux at 65 °C for 30 min. After hot filtration, the precipitated solid was cooled, filtered and dried to give 71 g of white crystalline pure product with HPLC purity greater than 98% and 34% yield.

[References]

[1] Patent: CN104725207, 2016, B. Location in patent: Paragraph 0068; 0069; 0070; 0071; 0072; 0073; 0074-0076
[2] Berichte der Bunsen-Gesellschaft, 1990, vol. 94, p. 497 - 513
[3] Chemische Berichte, 1906, vol. 39, p. 4125
[4] Journal of Organic Chemistry, 1954, vol. 19, p. 996,1000
[5] Tetrahedron, 1974, vol. 30, p. 3573 - 3581
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