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[ CAS No. 22934-58-3 ] {[proInfo.proName]}

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Chemical Structure| 22934-58-3
Chemical Structure| 22934-58-3
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Product Details of [ 22934-58-3 ]

CAS No. :22934-58-3 MDL No. :MFCD00266634
Formula : C10H10O5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 210.18 Pubchem ID :-
Synonyms :

Safety of [ 22934-58-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22934-58-3 ]

* 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 [ 22934-58-3 ]

[ 22934-58-3 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 3934-86-9 ]
  • [ 74-95-3 ]
  • [ 22934-58-3 ]
YieldReaction ConditionsOperation in experiment
98% With cesium fluoride; In N-methyl-acetamide; EXAMPLE 26 Methyl 3,4-methylenedioxy-5-methoxy-benzoate Cesium fluoride (24.5 g, 161.5 mmol) was added to a stirring solution of the phenol prepared in Example 25 (7.3 g, 36.8 mmol) in dimethylformamide (90 ml) under argon. After stirring 20 minutes, <strong>[74-95-3]dibromomethane</strong> (2.8 ml, 40.5 mmol) was added and the mixture heated for 2 hours. The reaction was allowed to cool to room temperature. Ether (300 ml) was added and the ethereal solution was washed with cold water (3 * 50 ml), dried and concentrated to afford the methylenedioxy derivative as a powder (7.62 g, 98%) yield, which was recrystallized from acetone-hexane, mp 89-91: IRnumax(NaCl) 1714, 1636, 1507, 1436, 1369, 1327, 1245, 1177, 1107, 1041, cmmin1; 1H-NMR (90 MHz) 3.89 (3H, s, OCH3), 6.06 (2H, s, &horbar;CH2&horbar;), 7.21 (1H, d, J = 1.4 Hz, ArH), 7.33 (1H, d, J = 1.4 Hz, ArH) and EIMS, m/z (rel. int/%) 210 (100, M+), 179, M+&horbar;OCH3).Anal. Calcd for C10H10O5: C, 57.15; H, 4.80 Found: C, 57.10; H, 4.74.
59% With potassium fluoride; In DMF (N,N-dimethyl-formamide); at 80℃; for 8h; Step 3) Methyl 3,4-dihydroxy-5-methoxybenzoate(48g, 240mmol) prepared in Step 2 was dissolved in dimethylformamide(1.2 litre), potassium fluoride (42g, 720mmol) and <strong>[74-95-3]dibromomethane</strong>(42.0g, 480mmol) were added thereto, and the mixture was heated while stirring for 8 hours at 80C. The reaction solution was cooled down to room temperature and the excess solvent was removed. The residue was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, concentrated and then subjected to silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3, v/v) to give methyl 7-methoxybenzo [3,4-d]1,3-dioxolan-5-carboxylate(30g, Yield 59%) as a white solid. 1H NMR (300MHz, CDCl3): delta 3.91(s, 3H), 3.96(s, 3H), 6.08(s, 2H), 7.24(d, 1H, J = 1.4Hz), 7.36(d, 1H, J = 1.4Hz)
  • 2
  • [ 22934-58-3 ]
  • [ 81474-46-6 ]
YieldReaction ConditionsOperation in experiment
51% With bromine; In acetic acid; REFERENTIAL EXAMPLE 3 In 35 ml of acetic acid was dissolved 10.5 g of methyl 5-methoxy-3,4-methylenedioxybenzoate, and a solution of bromine (formed by diluting 8 g of bromine with 25 ml of acetic acid) was dropped into the solution over a period of 1 hour. The mixture was stirred at room temperature for 10 hours and the reaction liquid was poured into ice water, and the formed precipitate was recovered by filtration and recrystallized from ethanol to obtain methyl 2-bromo-5-methoxy-3,4-methylenedioxybenzoate (the yield was 51%). Melting point: 103 to 105 C. Infrared absorption spectrum EQU3 cm-1 2944, 1726, 1626, 1488, 1462, 1434, 1404, 1326, 1248, 1194, 1176, 1108, 1040, 936 Proton nuclear magnetic resonance spectrum (delta ppm in CDCl3) 3.90 (s, 3H), 3.92 (s, 3H), 6.11 (s, 2H), 7.27 (s, 1H) Mass spectrum: m/z (%) 290 (89, M+), 288 (91, M+), 259 (100), 257 (100)
  • 3
  • [ 22934-58-3 ]
  • [ 111897-19-9 ]
  • 5
  • [ 77-78-1 ]
  • [ 116119-01-8 ]
  • [ 22934-58-3 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; Example 1 [0046] Preparation method of nitrogen-containing biphenyl compound of the present invention can be generally summarized as follows: [0047] Compound 3 (0.1 mmol) and Compound 4 (0.2-0.5 mmol) were put in a 25 mL round-bottomed flask, followed by addition of Pd(OAc)2 (0.01-0.05 mmol), Bu4NBr (0.15 mmol), K2CO3 (0.3 mmol) and 3 mL THF-H2O (VTHF/VH2O=1). The mixture was heated to 70 C. and the reaction was carried out for 4 hours. The reaction solution was cooled to room temperature, filtered, concentrated, and purified by silica gel column to give compounds 5-8 in Example 2-5. [0048] Compound 4 is purchased from Acros or Sigma-Aldrich Company. [0049] Compound 3 is obtained by the following synthetic route: [0050] (a) Synthesis of Bromo Compound 3: [0051] Bromo Compound 3 was synthesized using gallic acid as a starting material, through esterification of carboxyl group, etherification of phenolic hydroxyl group, bromination of benzene ring, removal of benzyl protecting group, and final methyl etherification. [0052] (b) Synthesis of Iodo Compound 3: [0053] Iodo Compound 3 was synthesized using one intermediate compound obtained during the synthesis of bromo Compound 3 as a starting material, through removal of benzyl protecting group, methyl etherification, nitration of benzene ring, reduction of nitro group into amino group, and final Sandmeyer reaction (amino group was firstly converted to a diazonium salt in the presence of concentrated HCl+NaNO2, and then, after the addition of an aqueous solution of KI, the iodo compound was obtained).
  • 6
  • [ 116119-01-8 ]
  • [ 74-88-4 ]
  • [ 22934-58-3 ]
YieldReaction ConditionsOperation in experiment
84% To a suspension of potassium carbonate(K2CO3) (211 mg, 1.53mmol) in dimethylsulfoxide (DMSO) (5 mL) was added a solution of compound A0061-2 (200 mg, 1.02 mmol) in DMSO (5 mL) and the mixture was stirred at room temperature for 30 minutes. Methyl iodide (217 mg, 1.53 mmol) was added, and the reaction mixture was stirred for another 4 hours. Methyl iodide was removed under reduced pressure and the residue obtained was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield compound A0061-3. (180mg, yield: 84%, 1H NMR confirmed) as a yellow solid.
  • 7
  • [ 607-91-0 ]
  • [ 22934-58-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrabutylammomium bromide; potassium hydroxide / 0.67 h / 100 °C 2.1: pyridine; ozone / methanol; chloroform / -15 - 0 °C 3.1: ammonium hydroxide; iodine / tetrahydrofuran; water / 16 h / 20 °C 3.2: 4 h / Reflux 4.1: thionyl chloride / 3 h / Reflux
Multi-step reaction with 4 steps 1: tetrabutylammomium bromide; potassium hydroxide / 0.67 h / 100 °C 2: pyridine; ozone / methanol; chloroform / -15 - 0 °C 3: urea hydrogen peroxide adduct; sodium hydroxide / methanol; water / Reflux 4: thionyl chloride / 3 h / Reflux
Multi-step reaction with 4 steps 1: potassium hydroxide / 0.67 h / 100 °C 2: ozone; pyridine / methanol; chloroform / -15 °C 3: urea hydrogen peroxide adduct / methanol / 1.5 h / Reflux 4: thionyl chloride / 1 h / Reflux
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