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Chemical Structure| 1667-01-2 Chemical Structure| 1667-01-2

Structure of 1667-01-2

Chemical Structure| 1667-01-2

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Product Details of [ 1667-01-2 ]

CAS No. :1667-01-2
Formula : C11H14O
M.W : 162.23
SMILES Code : CC(=O)C1=C(C)C=C(C)C=C1C
MDL No. :MFCD00008735
InChI Key :XWCIICLTKWRWCI-UHFFFAOYSA-N
Pubchem ID :15461

Safety of [ 1667-01-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1667-01-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1667-01-2 ]

[ 1667-01-2 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 60-29-7 ]
  • [ 4225-92-7 ]
  • [ 925-90-6 ]
  • [ 1667-01-2 ]
  • 2
  • [ 1667-01-2 ]
  • [ 4225-92-7 ]
YieldReaction ConditionsOperation in experiment
With bromine; In water; acetic acid; PREPARATION I 2-bromo-1-(2,4,6-trimethylphenyl)-1-ethanone (Compound 1) Dissolve 0.3 mol of 1-(2,4,6-trimethylphenyl)-1-ethanone in 200 ml of glacial acetic acid, and add 31.8 g of bromine dropwise while maintaining the reaction medium at a temperature below 10 C. When the addition is complete, allow the reaction medium to return to room temperature and leave at this temperature for 2 hours. Then pour the reaction medium into 500 ml of ice-cold water and extract the aqueous phase with ethyl ether. Wash the organic extracts with saturated aqueous sodium bicarbonate solution and then with salt water, and dry over anhydrous magnesium sulphate. After evaporation of the solvent, an oil is obtained, which may be used without further purification.
With copper(ll) bromide; In ethyl acetate; for 1.5h;Reflux; Synthesis of Exemplary Aminothiazoles and the Related Intermediates2-Bromo-1-mesitylethanone. To a solution of 1-mesitylethanone (1.02 g, 6.27 mmol) in EtOAc (50 mL) was added copper(II) bromide (CuBr2, 2.85 g, 12.8 mmol). The reaction mixture was heated at reflux for 90 min. The solution was allowed to cool down, and the resultant solids were filtered off and washed with EtOAc. The filtrate was concentrated under reduced pressure to give crude 2-bromo-1-mesitylethanone (1.67 g) as yellow oil: 1H NMR (500 MHz, CDCl3) delta 6.87 (2H, s), 4.27 (2 H, s), 2.31 (3H, s), 2.22 (6H, s).
With copper(ll) bromide; In ethyl acetate; for 1.5h;Reflux; To a solution of 1-mesitylethanone (1.02 g, 6.27 mmol) in EtOAc (50 mL) was added copper(II) bromide (CuBr2, 2.85 g, 12.8 mmol). Thereaction mixture was heated at reflux for 90 mm. The solution was allowed to cool down, andthe resultant solids were filtered off and washed with EtOAc. The filtrate was concentrated under reduced pressure to give crude 2-bromo-1-mesitylethanone (1.67 g) as yellow oil: 1H NMR (500 MHz, CDCl3) delta 6.87 (s, 2 H), 4.27 (s, 2H), 2.31 (s, 3 H), 2.22 (s, 6 H).
  • 3
  • [ 769-26-6 ]
  • [ 1667-01-2 ]
YieldReaction ConditionsOperation in experiment
80% With hydrogenchloride; water; copper(l) chloride; In methanol; at 20℃; for 6h;Irradiation; Inert atmosphere; General procedure: A 10 mL reaction vessel with a magnetic stirring bar was equipped with phenylacetylene (1 mmol), CuCl (1 mol%), HCl (0.2 mL, 37 wt %) and methanol (2 mL). The mixture was irradiated with a blue LED (5 W) and stirred under at r.t. in an air atmosphere for 6 h. The distance of the reaction vial from the light is about 2 centimeter. After the reaction, the solvent was removed under reduced pressure. Purification of the crude product was achieved by flash column chromatography using petrol ether/ethyl acetate (6:1~10:1) as eluent.
  • 4
  • [ 1667-01-2 ]
  • [ 4225-92-7 ]
  • [ 408511-50-2 ]
  • 5
  • [ 60-29-7 ]
  • [ 4225-92-7 ]
  • [ 71-43-2 ]
  • magnesium [ No CAS ]
  • [ 1667-01-2 ]
  • [ 412034-14-1 ]
  • 6
  • [ 4225-92-7 ]
  • [ 1667-01-2 ]
YieldReaction ConditionsOperation in experiment
53% With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; acetic acid; for 5.5h;Irradiation; Inert atmosphere; General procedure: Into a flask charged with the respective alpha-haloketone 2 (1 mmol) and ethidine (Hantzsch's ester, 1a; 1.2 mmol), was added the solvent as per Tables 2-4 (2.5 mL). The flask was then attached to a balloon filled with N2 and irradiated with 3 W blue LED at a distance of 5 cm. The workup was followed when TLC showed that ethidine or the haloketone was consumed. When AcOH was used as the solvent, the reaction was worked up as follows: the reaction mixture was partitioned between EtOAc (40 mL) and H2O (10 mL), then the organic phase was washed with sat. aq NaHCO3 (3 15 mL) and brine (15 mL), and dried (anhyd Na2SO4). After concentration under reduced pressure, the residue was subjected to flash chromatography for purification eluting with petroleum ether (PE) and CH2Cl2. When aprotic polar solvents were used, the reaction mixture was diluted with EtOAc (40 mL) and the organic layer was washed with H2O (3 15 mL) and brine (15 mL), and dried (anhyd Na2SO4). When volatile solvents were used, the mixture was concentrated under reduced pressure and the residue was subjected to flash chromatography for purification.
 

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