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Chemical Structure| 955929-56-3 Chemical Structure| 955929-56-3

Structure of 955929-56-3

Chemical Structure| 955929-56-3

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Product Details of [ 955929-56-3 ]

CAS No. :955929-56-3
Formula : C15H14O2
M.W : 226.27
SMILES Code : O=C(C1=CC(C2=C(C)C=CC=C2C)=CC=C1)O
MDL No. :MFCD11895286

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Application In Synthesis of [ 955929-56-3 ]

* 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 [ 955929-56-3 ]

[ 955929-56-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 955929-56-3 ]
  • [ 35418-07-6 ]
  • 3-(4-(2',6'-dimethyl-[1,1'-biphenyl]-3-carboxamido)phenyl)propanoic acid [ No CAS ]
  • 2
  • [ 955929-56-3 ]
  • [ 35418-07-6 ]
  • C25H25NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: To a solution of 3a (1 g) in ethanol was added Pd/C (5%, 0.1 g) and the mixture was stirred for 24 hrs at room temperature in a hydrogen atmosphere under atmospheric pressure. Insoluble matters were removed using Celite, and the filtrate was concentrated in vacuo to give the desired product 4a (0.76 g) as a yellow solid. To a solution of carboxylic acid (1 equiv) in CH2Cl2 (15 mL) at 0 C was added DMAP (1 equiv) and EDCI (1 equiv). The reaction mixture was stirred at 0 C for 45 minutes. At this time 4a (1 equiv) was added and the mixture was warmed to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo, partitioned between 1.0 M HCl (20 ml) and ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2 × 15 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v) as eluent to afford the product as a white solid. To a solution of the obtained solid (1 equiv) in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 2-17 as white solid.
  • 3
  • [ 691905-26-7 ]
  • [ 955929-56-3 ]
YieldReaction ConditionsOperation in experiment
76% With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; at 0 - 20℃; for 3h; To a solution of 7a (1 g, 4.8 mmol) in t-BuOH (3 mL) and THF (3 mL) were added 2-methylbut-2-ene (0.43 ml, 39 mmol) and NaH2PO4 (2.7 g, 20 mmol) at 0 C. Then NaClO2 (1.24 g, 13.7 mmol) and H2O (0.5 mL) were added sequentially. The resulting mixture was stirred at room temperature for 3 h. The reaction was quenched by the addition of brine (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to furnish the crude residue, which was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v, 1% acetic acid was added) as eluent to afford the product 8a (0.82 g, 76%) as a white solid.1H NMR (300 MHz, DMSO-d6) δ: 12.72 (brs, 1H), 7.88-7.92 (m, 1H), 7.66-7.68 (m, 1H), 7.61 (t, J = 7.5 Hz, 1H), 7.43-7.47 (m, 1H), 7.12-7.24 (m, 3H), 2.02 (s, 6H).
 

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