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Chemical Structure| 10268-12-9 Chemical Structure| 10268-12-9

Structure of 10268-12-9

Chemical Structure| 10268-12-9

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Product Details of [ 10268-12-9 ]

CAS No. :10268-12-9
Formula : C9H9NO4
M.W : 195.17
SMILES Code : COC(=O)CC1=CC(=CC=C1)[N+]([O-])=O
MDL No. :MFCD08669939
InChI Key :BFGYITRIATVARH-UHFFFAOYSA-N
Pubchem ID :526967

Safety of [ 10268-12-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 10268-12-9 ]

* 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 [ 10268-12-9 ]

[ 10268-12-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 124-41-4 ]
  • 3-Nitro-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one [ No CAS ]
  • [ 62621-09-4 ]
  • [ 10268-12-9 ]
  • 2
  • [ 10268-12-9 ]
  • [ 52022-77-2 ]
YieldReaction ConditionsOperation in experiment
90% [0438] A solution of methyl 2-(3-nitrophenyl)acetate (12 g, 62 mmol) in THF (100 ml) was cooled to 0 C, then MeOH (10 mL) was added slowly, followed by stirring at room temperature overnight. Water was added to terminate the reaction. The aqueous layer was extracted with ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give 2-(3- nitrophenyl)ethanol (9 g, yield 90%). 1H NMR: 400 MHz CDC13 delta 8.11-8.07 (m, 2H), 7.59-7.56 (m, 1H), 7.49-7.45 (m, 1H), 3.94-3.91 (m, 2H), 2.99-2.96 (m, 2H)
With sodium tetrahydroborate; In tetrahydrofuran; methanol; for 6h;Reflux; General procedure: To a mixture of LiAlH4 (15 mmol) in anhydrous THF (25 mL) in an ice-bath was added dropwise a solution of phenylacetic acids (15 mmol) in THF (8 mL). This mixture was stirred at room temperature for 30 min, and then heated to reflux for 4 h. After it was cooled to room temperature, water (0.5 mL) was added, and then NaOH (15%, 0.5 mL) and water (1.5 mL) were added in sequence. After stirring for another 30 min, the mixture was filtered, dried over anhydrous Na2SO4 and concentrated to give crude products. Pure phenylethyl alcohols were obtained in 50-85% yield by column chromatography. Alternative method: To a solution of phenylacetic acids (15 mmol) in MeOH (30 mL) was added SOCl2 (30 mmol). This mixture was heated to reflux for 3 h before evaporation. The residue was dissolved in DCM (30 mL), washed with aqueous NaHCO3, water and brine, dried over anhydrous Na2SO4, and concentrated to give 100% yield of crude methyl phenylacetates which were used to next step without further purification. To a solution of the methyl phenylacetates in THF (30 mL) was added NaBH4 (60 mmol). When the mixture was heated to gently reflux, MeOH (1.0 mL) was added dropwise from a syringe over 5 min. After refluxing for another 6 h, the mixture was cooled to room temperature and poured into 30 mL ice water, and extracted with EtOAc (30 mL × 2). The combined organic phase was washed with brine, dried over anhydrous Na2SO4, and concentrated to give crude products. Pure phenylethyl alcohols were obtained in 70-85% yield by column chromatography.
With methanol; sodium tetrahydroborate; In tetrahydrofuran; at 0 - 20℃; A solution of methyl 2-(3-nitrophenyl)acetate (Int 8a) (1 .20 g, 6.20 mmol) and NaBH (235 mg, 6.20 mmol) in THF (100 mL) was cooled to 0 C, then MeOH (10 mL) was added slowly, followed by stirring at rt overnight. Water was added to terminate the reaction. The aqueous layer was extracted with ethyl acetate 3 times, the combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give the title compound as a yellow solid.
 

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