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Chemical Structure| 273200-57-0

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Product Details of [ 273200-57-0 ]

CAS No. :273200-57-0
Formula : C15H14O3
M.W : 242.27
SMILES Code : O=CC1=CC=CC(OCC2=CC=CC=C2)=C1OC
MDL No. :MFCD22041844

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* 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 [ 273200-57-0 ]

[ 273200-57-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 66495-88-3 ]
  • [ 100-39-0 ]
  • [ 273200-57-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;potassium iodide; In DMF (N,N-dimethyl-formamide); at 20℃; for 17h; To a solution of the compound (11.4 g) obtained in the aforementioned (1), potassium carbonate (22.8 g) and potassium iodide (2.49 g) in DMF (130 ml) was added benzyl bromide (9.8 ml), and the mixture was stirred at room temperature for 17 hrs. The obtained reaction mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate (1500 ml) and water (1500 ml). The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography and crystallized from diisopropyl ether and hexane to give 3-benzyloxy-2-methoxybenzaldehyde (13.7 g) as pale-yellow crystals. 1H-NMR (CDCl3) δ:4.03 (3H, s), 5.16 (2H, s), 7.09-7.47 (8H, m), 10.45 (1H, d, J = 0.66 Hz).
With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 20℃; for 17h; Reference Example 2 3-Benzyloxy-2-methoxybenzaldehyde To a solution of the compound obtained in Reference Example 1 (11.4 g), potassium carbonate (22.8 g) and potassium iodide (2.49 g) in DMF (130 ml) was added benzyl bromide (9.8 ml), and the mixture was stirred at room temperature for 17 hours. The resulting reaction mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate (1500 ml) and water (1500 ml). The organic layer was washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, and crystallized using diisopropyl ether and hexane to obtain the title compound (13.7 g) as a pale yellow crystal. 1H-NMR (CDCl3) δ: 4.03 (3H, s), 5.16 (2H, s), 7.09-7.47 (8H, m), 10.45 (1H, d, J = 0.66 Hz).
With potassium carbonate; In N,N-dimethyl-formamide; at 40℃; for 2.5h;Inert atmosphere; [0309] Int60 (17 g, 111 mmol) is mixed with dry DMF (280 mL) and K2CO3 (23 g, 167 mmol), under N2 atmosphere. Benzyl bromide (16.5 mL, 139 mmol) is added in one portion. The mixture is stirred at 40C for 2.5 h, cooled to room temperature and treated with H2O (0.5 L) and toluene (0.5 L). The resulting layers are separated, and the aqueous layer is extracted again with toluene (0.25 L). The combined organic layer is washed with 3x0.25 L H2O, dried on Na2SO4, filtered and evaporated in vacuo. The residue is treated with light petroleum ether (100 mL) and stirred until powdery. The suspension is filtered on Buchner, the solid is washed with light petroleum ether (50 mL), dried under suction and then in vacuo at 40C to yield the desired product.
 

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