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CAS No. : | 131170-40-6 | MDL No. : | MFCD06408344 |
Formula : | C11H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MJEMBQXUGUQDEK-UHFFFAOYSA-N |
M.W : | 176.21 | Pubchem ID : | 3652665 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; potassium <i>tert</i>-butylate 1) hexane, 2h; Yield given. Multistep reaction. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 74 percent / Na, EtOH / Heating 2: 1) BuLi, tert-BuOK / 1) hexane, 2h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Stage #1: 2-methyl-4-(1-methylcyclopropyl)benzoic acid With thionyl chloride In dichloromethane at 0℃; for 2h; Stage #2: 3-bromo-2-[[tert-butyl(dimethyl)silyl]oxymethyl] aniline With triethylamine In dichloromethane at 0 - 20℃; for 12h; | Step-d: Synthesis of N-(3-bromo-2-(((tert-butyldimethylsilyl) oxy) methyl) phenyl)-4-(l- methylcyclopropyPbenzamide To a stirred solution of 4-(l-methylcyclopropyl) benzoic acid (0.156 g, 0.88 mmol) in DCM (10 ml) was added thionyl chloride (0.7 ml) at 0°C. The reaction mixture was allowed to stir at 0°C for 2 h. Solvent was concentrated under reduced pressure, the residue obtained was re- dissolved in DCM (10 ml) and cooled to 0°C. Then TEA (0.5 ml. 3.79 mmol) and 3-bromo-2- (((tert-butyldimethylsilyl)oxy)methyl)aniline (0.2 g, 0.632 mmol) were added. The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with ice water and the product was extracted with DCM. The organic layer dried and concentrated. The crude material obtained was purified using column chromatography eluted in 2% EtOAc-hexane to afford the title compound (0.2 g, 66 %). 1H NMR (400 MHz, DMSO-d6) δ 9.91 (s, 1H), 8.34 (d, J=7.6 Hz, 1H), 7.86 (d, J=8.4 Hz, 2H), 7.32-7.26 (m, 3H), 7.22 (t, Ji=8.4 Hz, J2=7.6 Hz, 1H), 5.10 (s, 2H), 1.59 (s, 3H), 0.94-0.81 (m, 13H), 0.15 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,4-dioxane / 6 h / 110 °C / Sealed tube; Inert atmosphere 2.1: diethylzinc; trifluoroacetic acid / dichloromethane; n-heptane / 0.33 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: diethylzinc; trifluoroacetic acid / dichloromethane; n-heptane / 0.33 h / 0 °C 1.2: 16 h / 0 - 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57.97% | With lithium hydroxide monohydrate; water In tetrahydrofuran; methanol at 20℃; for 12h; | Step-c: Synthesis of 4-(l-methylcyclopropyl) benzoic acid To a stirred solution of methyl 4-(l-methylcyclopropyl) benzoate (0.15 g, 0.78 mmol) in MeOH (10 ml), THF (2 ml) and water (1 ml) was added lithium hydroxide monohydrate (0.1 g, 2.36 mmol). The reaction mixture was stirred at RT for a period of 12 h. The excess solvent was concentrated under reduced pressure; the residue was dissolved in water and acidified with IN HC1. The precipitated solid was collected by filtration to afford the title compound (0.080 g, 57.97 %). *H NMR (400 MHz, DMSO-d6) δ 12.76 (s, 1H), 7.85 (d, J=8.3 Hz, 2H), 7.31 (d, J=8.3 Hz, 2H), 1.40 (s, 3H), 0.93-0.82 (m, 4H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / water; tetrahydrofuran / 2 h / 80 °C 2: diethylzinc; diiodomethane / dichloromethane; toluene / 16 h / 20 °C 3: water; lithium hydroxide / 1,4-dioxane / 1 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: diethylzinc; diiodomethane / dichloromethane; toluene / 16 h / 20 °C 2: water; lithium hydroxide / 1,4-dioxane / 1 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.9% | With water; lithium hydroxide In 1,4-dioxane at 15℃; for 1h; | 339.2 Methyl 2-methyl-4-(1-methylcyclopropyl)benzoate (80.0 mg, 0.39 mmol) was hydrolyzed as usual (General Method NaOH) to afford 2-methyl-4-(1- methylcyclopropyl)benzoic acid (70 mg, 93.9% yield) as a white solid. ‘H NMR (400 MHz,CD3OD): 7.83 (d, I = 8.0 Hz, 1H), 7.15 - 7.10 (m, 2H), 2.56 (s, 3H), 1.42 (s, 3H), 0.95 - 0.85 (m, 2H), 0.85 - 0.75 (m, 2H). |