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Chemical Structure| 334018-24-5 Chemical Structure| 334018-24-5

Structure of 334018-24-5

Chemical Structure| 334018-24-5

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Product Details of [ 334018-24-5 ]

CAS No. :334018-24-5
Formula : C8H9ClO2
M.W : 172.61
SMILES Code : OCC1=CC=C(OC)C=C1Cl
MDL No. :MFCD16037274

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Application In Synthesis of [ 334018-24-5 ]

* 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 [ 334018-24-5 ]

[ 334018-24-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 54439-75-7 ]
  • [ 334018-24-5 ]
YieldReaction ConditionsOperation in experiment
97% With sodium borohydrid; In methanol; ethyl acetate; Reference Example 21 2-chloro-4-methoxybenzyl alcohol To a solution of <strong>[54439-75-7]2-<strong>[54439-75-7]chloro-4-methoxybenzaldehyde</strong></strong> (1.55 g, 9 mmol) in methanol (20 mL) was added under ice-cooling sodium borohydride (378 mg, 10 mmol) and the mixture was stirred atroom temperature for 30 min. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an almost pure title compound (1.5 g, 97percent). 1H-NMR (delta ppm, CDCl3): 1.87 (1H, br t, J=6.2 Hz), 3.80 (3H, s), 4.71 (2H, d, J=5.8 Hz), 6.81 (1H, dd, J=2.6, 8.6 Hz), 6.93 (1H, d, J=2.6 Hz), 7.35 (1H, d, J=8.4 Hz)
94.2% To the solution of compound E2 (10 g, 61.8 mmol) in 100 mL of EtOH was added NaBH4 (5.0 g, 123.6 mmol), and the mixture was stirred at room temperature for 2 h under N2 atmosphere. 1 N HCI solution was added for quench. The reaction mixture was concentrated under reduced pressure and EtOAc was added to extract twice. The combined organic layers were washed with water and brine consecutively, dried over Na2SO4, filtered, concentrated and purified by chromatography on silica gel (eluent: PE/EA = 2/1) to give 10 g of compound E3 as an oil (Yield: 94.2percent).
With sodium tetrahydroborate; In ethanol; at 20℃; Acetonitrile (70 ml), potassium carbonate (1.7 g, 12.3 mmol) and methyl iodide (0.71 ml, 12.3 mmol) were added to 2-chloro-4-hydroxybenzaldehyde (1.5 g, 9.6 mmol), and the mixture was stirred overnight at 50° C. A treatment according to a conventional method using ethyl acetate as an extraction solvent gave a crude product. The obtained crude product was dissolved in ethanol (30 ml) and sodium borohydride (433 mg, 9.6 mmol) were added, and the mixture was stirred overnight at room temperature. A treatment according to a conventional method using ethyl acetate as an extraction solvent gave a crude product. The obtained crude product was dissolved in thionyl chloride (5 ml) and, after stirring at room temperature for 4 hr, treated according to a conventional method using ethyl acetate as an extraction solvent. The obtained crude product was dissolved in dimethyl sulfoxide (30 ml), sodium cyanide (470 mg, 9.6 mmol) was added, and the mixture was stirred overnight at room temperature. A treatment according to a conventional method using ethyl acetate as an extraction solvent gave a crude product, which was successively purified by silica gel column chromatography to give a nitrile intermediate (770 mg, 4.25 mmol). 1H-NMR (300 MHz, CDCl3) delta 3.76 (2H, s), 3.81 (3H, s), 6.84 (1H, dd), 6.96 (1H, d), 7.38 (1H, d)
 

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