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Chemical Structure| 55171-76-1 Chemical Structure| 55171-76-1

Structure of 55171-76-1

Chemical Structure| 55171-76-1

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Product Details of [ 55171-76-1 ]

CAS No. :55171-76-1
Formula : C10H10O3
M.W : 178.18
SMILES Code : O=C1C2=CC(OC)=C(OC)C=C2C1

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Application In Synthesis of [ 55171-76-1 ]

* 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 [ 55171-76-1 ]

[ 55171-76-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 55171-76-1 ]
  • [ 38622-91-2 ]
  • [ 35202-54-1 ]
YieldReaction ConditionsOperation in experiment
54% Example 3 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile A solution of TosMIC (0.98 g, 4.98 mmol, 2.3 eq) in THF (3 mL) is poured, over 20 minutes, into a solution of potassium tert-butoxide (1.22 g; 10.9 mmol; 5 eq) in THF (7.5 mL) stirred at 0° C. under nitrogen. Then 200 muL of methanol are added to the mixture and stirring is maintained for 30 minutes at 0° C. In parallel, 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one (0.39 g, 2.17 mmol, 1 eq), lithium bromide (0.19 g, 2.17 mmol, 1 eq) and THF (2.5 mL) are transferred into a second three-necked flask. After cooling to 0° C. under nitrogen, the solution of TosMIC and potassium tert-butoxide is transferred to the reaction mixture. After returning to ambient temperature, the solution is heated to 40° C. and stirred for 16 hours at that temperature. The mixture is then hydrolysed with a solution of 11N HCl (0.7 mL, 7.73 mmol) in water (2 mL). After evaporating off the THF under reduced pressure, the product is extracted with 5 mL of dichloromethane. The organic phase is washed twice with 2*5 mL of water before being dried. The crude product is purified by column chromatography over silica gel using the binary mixture methylcyclohexane/ethyl acetate 75/25 to obtain the title product in the form of a cream-coloured powder. Yield=54percent 1H NMR (CDCl3): 6.76 (s; 1H); 6.68 (s; 1H); 4.14 (m; 1H); 3.83 (s; 6H); 3.59-3.41 (m; 2H). 13C NMR (CDCl3): 151.4; 150.4; 134.2; 129.7; 119.9; 106.9; 106.1; 56.2; 35.5; 22.6.
 

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