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Chemical Structure| 54544-05-7

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Product Details of [ 54544-05-7 ]

CAS No. :54544-05-7
Formula : C22H20O4
M.W : 348.39
SMILES Code : O=C(OC)C1=CC=C(OCC2=CC=CC=C2)C(OCC3=CC=CC=C3)=C1
MDL No. :MFCD06203841
InChI Key :SLYKXRFTRIYUJV-UHFFFAOYSA-N
Pubchem ID :10545660

Safety of [ 54544-05-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 54544-05-7 ]

* 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 [ 54544-05-7 ]

[ 54544-05-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 54544-05-7 ]
  • [ 1570-05-4 ]
YieldReaction ConditionsOperation in experiment
74% With sodium hydroxide; water; In methanol; for 4h;Heating / reflux; C) 3, 4-Dibenzyloxy benzoic acid; A solution of sodium hydroxide (1.2 g) in methanol (100 ml) was added to a solution of 3,4-dibenzyloxy benzoic acid methyl ester (4.64 g) in methanol (50 ml) and refluxed for 4 hrs. After removal of methanol under reduced pressure the residue was dissolved in water (100 ml) and washed with ethyl acetate (2 x 50 ml). The aqueous layer was acidified with 2N hydrochloric acid to pH 2. The precipitated product was collected by filtration which on drying under vacuum provided 2.4 g of 3,4-benzyloxy benzoic acid. (Yield = 74%) 'H NMR CDC13 7.7 (2H, b, s) 7.27-7.5 (10H, m) 6.98 (lH, d, J 8Hz) 5.26 (2H, s) 5.22 (2H, s)
32.2 g With sodium hydroxide; In tetrahydrofuran; methanol; water; at 80℃; for 1h; To a solution of 8b (15.0 g, 97.4 mmol) in MeOH (360 mL) was added SOCl2 (7.9 mL, 48.7 mmol) fordropwise at 60 C. The reaction mixture was stirred at 60 C for 10 h. Then, the reaction mixture wasevaporated under reduced pressure. The crude mixture was applied to following reaction without furtherpurification.To a mixture of crude residue and K2CO3 (40.4 g, 0.292 mol) in DMF (162 mL) was added benzylbromide (29.0 mL, 0.244 mol) at 100 C. The reaction mixture was stirred at 100 C for 16 h. Then, thereaction mixture was filtered through a pad of Celite, diluted with H2O, and extracted with EtOAc. Theorganic layer was washed with water and brine, dried over anhydrous MgSO4, and evaporated underreduced pressure. The crude mixture was applied to following reaction without further purification.To a stirred solution of crude residue in MeOH/THF (1/1, 324 mL) were added 4 M NaOH aq. (85 mL,0.34 mol) at 80 C. The reaction mixture was stirred at same temperature for 1 h. Then, the reactionmixture was quenched with 6 M HCl aq., filtered and washed with H2O to give 9b (32.2 g, 96.3 mmol,99%) as a white solid.Spectral data for 9b were in good agreement with those reported in reference.16
With sodium chlorite; sodium hydrogenphosphate dodecahydrate; dihydrogen peroxide; In water; acetonitrile; at 20℃; for 2h; General procedure: The compound 2a (4.7 mmol) was dissolved in the mixed solvent (MeCN/H2O, 5:1, V/V), added NaClO2 (687.0 mg), NaH2PO4.12H2O (883.8 mg) and H2O2 (3.0 mL), then the reaction mixture was stirred for 2 h at room temperature. After completion of the reaction, the solution was acidified with 1 mol/L HCl, extracted with ethyl acetate, and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to provide the yellow residue, which was used directly in the next step without purification and structural characterization.
 

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