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Chemical Structure| 27023-05-8 Chemical Structure| 27023-05-8

Structure of 27023-05-8

Chemical Structure| 27023-05-8

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Product Details of [ 27023-05-8 ]

CAS No. :27023-05-8
Formula : C10H12O3
M.W : 180.20
SMILES Code : O=C(OC)C1=CC(C)=C(O)C=C1C
English Name :Methyl 4-hydroxy-2,5-dimethylbenzoate
MDL No. :MFCD13659356

Safety of [ 27023-05-8 ]

Application In Synthesis of [ 27023-05-8 ]

* 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 [ 27023-05-8 ]

[ 27023-05-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 67-56-1 ]
  • [ 114971-53-8 ]
  • [ 27023-05-8 ]
YieldReaction ConditionsOperation in experiment
With carbon monoxide; triethylamine In dimethyl sulfoxide 16 Methyl 2,5-dimethyl-4-trifluoromethanesulfonyloxybenzoate Reference Example 16; Methyl 2,5-dimethyl-4-trifluoromethanesulfonyloxybenzoate; A mixture of 4-iodo-2,5-dimethylphenol (1.0g), palladium acetate (0.045g), 1,3-bis(diphenylphosphino)propane (0.083g), triethylamine (0.90mL), methanol (20mL) and dimethylsulfoxide (30mL) was stirred at 60° C overnight under an atmosphere of carbon monooxide. The insoluble materials were removed by filtration, and the filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1-3/1) to afford methyl 4-hydroxy-2,5-dimethylbenzoate (0.16g).1H-NMR(CDCl3)δ ppm: 2.23 (3H; s), 2.53 (3H, s), 3.85 (3H, s), 4.94 (1H, br s), 6.62 (1H, s), 7.77 (1H, s) Trifluoromethanesulfonic anhydride (0.27g) was added to an ice-cooled mixture of methyl 4-hydroxy-2,5-dimethylbenzoate (0.144g) and pyridine (0.095g) in methylene chloride (10mL) with stirring. The mixture was stirred at room temperature for 30min, and poured into a mixture of ethyl acetate and 2mol/L hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane: ethyl acetate=10/1) to afford the title compound (0.226g).1H-NMR(CDCl3)δ ppm: 2.36 (3H, s), 2.58 (3H, s), 3.90 (3H, s), 7.12 (1H, s), 7.87 (1H, s)
  • 2
  • [ 13730-55-7 ]
  • [ 27023-05-8 ]
  • [ 27023-04-7 ]
  • [ 3921-13-9 ]
YieldReaction ConditionsOperation in experiment
1: 25% 2: 13% 3: 13% Stage #1: methyl 2,5-dimethylbenzoate With 6,7-dichlorobenzo[d][1,2]dioxine-1,4-dione at 75℃; for 48h; Stage #2: With water; sodium hydrogencarbonate In methanol at 50℃; for 1h; Inert atmosphere; Overall yield = 51 %; regioselective reaction;
 

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