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Chemical Structure| 61227-22-3 Chemical Structure| 61227-22-3

Structure of 61227-22-3

Chemical Structure| 61227-22-3

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Product Details of [ 61227-22-3 ]

CAS No. :61227-22-3
Formula : C15H14O4
M.W : 258.27
SMILES Code : COC(=O)C1=C(O)C=CC(OCC2=CC=CC=C2)=C1
MDL No. :MFCD20441274

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Application In Synthesis of [ 61227-22-3 ]

* 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 [ 61227-22-3 ]

[ 61227-22-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 2150-46-1 ]
  • [ 100-39-0 ]
  • [ 61227-22-3 ]
YieldReaction ConditionsOperation in experiment
69% With potassium carbonate; In methanol; chloroform; for 4.5h;Reflux; Methyl 5-(benzyloxy)-2-hyd roxybenzoateOHOBnBr, K2003 C H Cl 3/C H 30 HTo a refluxed suspension of K2C03 (32.8 g, 238 mmol) in methanol (180 mL) andCHCI3 (350 mL) was then added a mixture of methyl 2,5-dihydroxybenzoate (10.0 g,59.5 mmol) and bromomethylbenzene (7.10 mL, 59.5 mmol) in methanol/CHCI3 (50mL/25 mL) drop wise over 30 minutes. The resulting mixture was stirred at reflux for another 4 hours. After cooling down and filtration, the filter cake was washed with CHCI3 (20 mL). The combined filtrate was concentrated under reduced pressure. The residue was redissolved in CHCI3 (200 mL), washed with HCI (1 N) (100 mL x 2). Theorganic was then washed with brine (100 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography eluting with petroleum ether/EtOAc (8: 1) to give methyl 5-(benzyloxy)-2-hydroxybenzoate (10.6 g, 69.0%) as a white solid.1H NMR (500 MHz, DMSO-d6) ö10.09(s, 1H), 7.43 (d, J= 7.2 Hz, 2H), 7.40-7.36 (m,2H), 7.34-7.32 (2H, m), 7.23 (dd, J= 9.2, 3.2 Hz, 1H), 6.93 (d, J= 9.2 Hz, 1H), 5.06 (5, 2H), 3.88 (5, 3H). NOESY showed the desired product as well.
69% With potassium carbonate; In methanol; chloroform; for 4.5h;Reflux; To a refluxed suspension of K2CO3 (32.8 g, 238 mmol) in methanol (180 mL) and CHCl3 (350 mL) was then added a mixture of methyl 2,5-dihydroxybenzoate (10.0 g, 59.5 mmol) and bromomethylbenzene (7.10 mL, 59.5 mmol) in methanol/CHCl3 (50 mL/25 mL) drop wise over 30 minutes. The resulting mixture was stirred at reflux for another 4 hours. After cooling down and filtration, the filter cake was washed with CHCl3 (20 mL). The combined filtrate was concentrated under reduced pressure. The residue was redissolved in CHCl3 (200 mL), washed with HCl (1N) (100 mL*2). The organic was then washed with brine (100 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography eluting with petroleum ether/EtOAc (8:1) to give methyl 5-(benzyloxy)-2-hydroxybenzoate (10.6 g, 69.0%) as a white solid. 1H NMR (500 MHz DMSO-d6) δ 10.09 (s, 1H), 7.43 (d, J=7.2 Hz, 2H), 7.40-7.36 (m, 2H), 7.34-7.32 (2H, m), 7.23 (dd, J=9.2, 3.2 Hz, 1H), 6.93 (d, J=9.2 Hz, 1H), 5.06 (s, 2H), 3.88 (s, 3H). NOESY showed the desired product as well.
69% With potassium carbonate; In methanol; chloroform; for 4.5h;Reflux; To a refluxed suspension of K2CO3 (32.8 g, 238 mmol) in methanol (180 mL) and CHCI3 (350 mL) was then added a mixture of methyl 2,5-dihydroxybenzoate (10.0 g, 59.5 mmol) and bromomethylbenzene (7.10 mL, 59.5 mmol) in methanol/CHCl3 (50 mL/25 mL) drop wise over 30 minutes. The resulting mixture was stirred at reflux for another 4 hours. After cooling down and filtration, the filter cake was washed with CHCI3 (20 mL). The combined filtrate was concentrated under reduced pressure. The residue was redissolved in CHCI3 (200 mL), washed with HCI (1 N) (100 mL x 2). The organic was then washed with brine (100 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography eluting with petroleum ether/EtOAc (8: 1 ) to give methyl 5-(benzyloxy)-2-hydroxybenzoate (10.6 g, 69.0%) as a white solid. 1H NMR (500 MHz, DMSO-c/6) δ 10.09 (s, 1 H), 7.43 (d, J = 7.2 Hz, 2H), 7.40-7.36 (m, 2H), 7.34-7.32 (2H, m), 7.23 (dd, J = 9.2, 3.2 Hz, 1 H), 6.93 (d, J = 9.2 Hz, 1 H), 5.06 (s, 2H), 3.88 (s, 3H). NOESY showed the desired product as well.
69% With potassium carbonate; In methanol; chloroform; for 4.5h;Reflux; To a refluxed suspension of K2CO3 (32.8 g, 238 mmol) in methanol (180 mL) and CHCl3 (350 mL) was then added a mixture of methyl 2,5-dihydroxybenzoate (10.0 g, 59.5 mmol) and bromomethylbenzene (7.10 mL, 59.5 mmol) in methanol/CHCl3 (50 mL/25 mL) drop wise over 30 minutes. The resulting mixture was stirred at reflux for another 4 hours. After cooling down and filtration, the filter cake was washed with CHCl3 (20 mL). The combined filtrate was concentrated under reduced pressure. The residue was redissolved in CHCl3 (200 mL), washed with HCl (1N) (100 mL*2). The organic was then washed with brine (100 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography eluting with petroleum ether/EtOAc (8:1) to give methyl 5-(benzyloxy)-2-hydroxybenzoate (10.6 g, 69.0%) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 10.09 (s, 1H), 7.43 (d, J=7.2 Hz, 2H), 7.40-7.36 (m, 2H), 7.34-7.32 (2H, m), 7.23 (dd, J=9.2, 3.2 Hz, 1H), 6.93 (d, J=9.2 Hz, 1H), 5.06 (s, 2H), 3.88 (s, 3H). NOESY showed the desired product as well.
63% With potassium carbonate; In acetone; at 20℃; (Step 1) To a mixed solution of methyl 2,5-dihydroxybenzoate (10.0 g), potassium carbonate (12.3 g) and acetone (100 ml) was added benzyl bromide (7.43 ml), and the mixture was stirred overnight at room temperature. After the insoluble material was removed by filtration, the mother solution was concentrated. The obtained residue was purified by column chromatography (LL, Biotage cartridge, ethyl acetate:n-hexane=1:9→1:5) to give methyl 5-benzyloxy-2-hydroxybenzoate (9.63 g, 63%) as colorless crystals.
53% With potassium carbonate; In methanol; chloroform; at 70℃; for 3h; [00287] To a solution of Example 18a (11.0 g, 65.47 mmol) in CHCl3/MeOH (300 mL/150 mL) was added K2C03 (27.0 g, 196.41 mmol). Then BnBr (11.0 g, 65.47 mmol) was added into the mixture at 70C and the mixture was stirred at the same temperaturefor 3 h. The mixture was filtrated and the filtratewas concentrated under reduced pressure. The residue was purified by silica gel chromatography (Petroleum Ether/EtOAc = 100/1 to 10/1) to give the desired product Example 18b (9.0 g, yield 53%) as a white solid. LCMS [M+l]+ = 259.0
30% With potassium carbonate; at 60℃; for 8h; To a stirred solution of methyl 2,5-dihydroxybenzoate (1 g, 5.95 mmol) in chloroform and methanol, were added K2CO3 (3.3 g, 23.8 mmol) and benzyl bromide (0.85 mL, 7.14 mmol). The reaction mixture was then stirred for 8 h at 60 C. Upon completion of reaction, the mixture was concentrated under vacuum, diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated. The crude product thus obtained was purified by flash column chromatography to obtain methyl 5-(benzyloxy)-2-hydroxybenzoate (470 mg, yield: 30 %) as a colourless liquid.1H NMR (400 MHz, DMSO-d6): δ 10.09 (s, 1H), 7.43 (d, J = 7.2 Hz, 2H), 7.38 (t, J = 7.2 Hz, 2H), 7.33 - 7.29 (m, 2H), 7.24 - 7.21 (m, 1H), 6.93 (d, J = 8.8 Hz, 1H), 5.05 (s, 2H), 3.88 (s, 3H). LC-MS (m/z): 259.07 (M+H)+

 

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