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CAS No. : | 2065-27-2 | MDL No. : | MFCD00075861 |
Formula : | C10H12O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XLXVNKPXOIYLLE-UHFFFAOYSA-N |
M.W : | 196.20 | Pubchem ID : | 137419 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
94% | With sulfuric acid for 18h; Reflux; | |
92% | With sulfuric acid at 0℃; for 16h; Reflux; | |
77% | With di(methoxycarbonyl)methylene tri-n-butylphosphorane In toluene at 70℃; for 24h; |
77% | In toluene | |
65% | With sulfuric acid at 70℃; for 2h; | |
With hydrogenchloride | ||
Stage #1: 2-6-dimethoxybenzoic acid With oxalyl dichloride In N,N-dimethyl-formamide for 1h; Heating; Stage #2: methanol With triethylamine at 20℃; for 0.166667h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium; <i>tert</i>-butyl alcohol 1.) THF, ammonia, -78 deg C, 15 min; 2.) THF, -33 deg C; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In diethyl ether for 0.166667h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium carbonate In acetone for 23h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Stage #1: methyl 2,6-dimethoxybenzoate With potassium In tetrahydrofuran; ammonia; <i>tert</i>-butyl alcohol Stage #2: methyl iodide Further stages.; | |
With ammonia; <i>tert</i>-butyl alcohol 1) THF, -78 deg C, 2) -78 deg C; Multistep reaction; | ||
With penta-1,3-diene; potassium <i>tert</i>-butylate; ammonia; potassium 1.) THF, t-butyl alcohol, -70 deg C 2.) THF; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With ammonia In <i>tert</i>-butyl alcohol at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With 1,8-diazabicyclo[5.4.0]undec-7-ene for 4h; Heating; | |
98% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 160℃; for 0.2h; microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | Stage #1: 2-methylquinoline With n-butyllithium In diethyl ether; hexane at -10℃; for 2h; Stage #2: methyl 2,6-dimethoxybenzoate In diethyl ether; hexane at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In various solvent(s) at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: methyl 2,6-dimethoxybenzoate With ammonia; sodium In diethyl ether; <i>tert</i>-butyl alcohol Stage #2: allyl bromide In diethyl ether; <i>tert</i>-butyl alcohol at -78 - 20℃; for 11h; Further stages.; | ||
Stage #1: methyl 2,6-dimethoxybenzoate With ammonia; sodium; <i>tert</i>-butyl alcohol In diethyl ether at -78℃; for 0.5h; Inert atmosphere; Stage #2: allyl bromide In diethyl ether | ||
With ammonia; sodium In diethyl ether; <i>tert</i>-butyl alcohol at -78℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: BCl3 / CH2Cl2 / 21.5 h / 0 °C 1.2: 90 percent / Solvolysis 2.1: NaH / dimethylformamide / 3.67 h / 0 - 20 °C 3.1: Grignard reagent 3.2: ZnCl2 / tetrahydrofuran / 0.33 h / 0 °C 3.3: Pd2(dba)3; 1,1'-bis(diphenylphosphino)ferrocene / tetrahydrofuran / 4.5 h / 60 °C 4.1: 4 percent / iodine / acetonitrile / 1.5 h / 52 - 57 °C | ||
Multi-step reaction with 5 steps 1.1: BCl3 / CH2Cl2 / 21.5 h / 0 °C 1.2: 90 percent / Solvolysis 2.1: NaH / dimethylformamide / 3.67 h / 0 - 20 °C 3.1: Grignard reagent 3.2: ZnCl2 / tetrahydrofuran / 0.33 h / 0 °C 3.3: Pd2(dba)3; 1,1'-bis(diphenylphosphino)ferrocene / tetrahydrofuran / 4.5 h / 60 °C 4.1: 24 percent / iodine / acetonitrile / 1.5 h / 52 - 57 °C 5.1: 93 percent / Et3N; PPh3; 99 percent formic acid / Pd(OAc)2 / dimethylformamide / 5 h / 60 °C | ||
Multi-step reaction with 5 steps 1.1: BCl3 / CH2Cl2 / 21.5 h / 0 °C 1.2: 90 percent / Solvolysis 2.1: NaH / dimethylformamide / 3.67 h / 0 - 20 °C 3.1: Grignard reagent 3.2: ZnCl2 / tetrahydrofuran / 0.33 h / 0 °C 3.3: Pd2(dba)3; 1,1'-bis(diphenylphosphino)ferrocene / tetrahydrofuran / 4.5 h / 60 °C 4.1: 89 percent / iodine / acetonitrile / 3 h / 20 °C 5.1: 93 percent / Et3N; PPh3; 99 percent formic acid / Pd(OAc)2 / dimethylformamide / 5 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH2Cl2 / Ambient temperature 5: 88 percent / K2CO3 / acetone / 120 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH2Cl2 / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH4 / methanol / 0.2 h / 0 °C 7: 87 percent / PBr3, pyridine / benzene / 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH4 / methanol / 0.2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH4 / methanol / 0.2 h / 0 °C 7: 87 percent / PBr3, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH2Cl2 / Ambient temperature 5: 88 percent / K2CO3 / acetone / 120 h / Heating 6: 88 percent / KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH2Cl2 / Ambient temperature 5: 88 percent / K2CO3 / acetone / 120 h / Heating 6: 88 percent / KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h 7: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 8: 100 percent / NaBH4 / methanol / 0.25 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH2Cl2 / Ambient temperature 5: 88 percent / K2CO3 / acetone / 120 h / Heating 6: 88 percent / KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h 7: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 8: 100 percent / NaBH4 / methanol / 0.25 h / 0 °C 9: 96 percent / PBr3, pyridine / benzene / 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH2Cl2 / Ambient temperature 5: 88 percent / K2CO3 / acetone / 120 h / Heating 6: 88 percent / KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h 7: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH2Cl2 / Ambient temperature 5: 88 percent / K2CO3 / acetone / 120 h / Heating 6: 88 percent / KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h 7: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 8: 100 percent / NaBH4 / methanol / 0.25 h / 0 °C 9: 96 percent / PBr3, pyridine / benzene / 3 h 10: 91 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 14 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH4 / methanol / 0.2 h / 0 °C 7: 87 percent / PBr3, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 9: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h 10: 41 percent / BF3 / nitromethane / 2 h / -30 °C 12: 91 percent / m-CPBA / CH2Cl2 / 1 h / -78 °C 13: 82 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature 14: 1) TiCl4, glacial acetic acid, 2) H2O / 1) 20 min, 2) reflux, 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH4 / methanol / 0.2 h / 0 °C 7: 87 percent / PBr3, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 9: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: m-CPBA / CH2Cl2 / Ambient temperature 5: 88 percent / K2CO3 / acetone / 120 h / Heating 6: 88 percent / KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h 7: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 8: 100 percent / NaBH4 / methanol / 0.25 h / 0 °C 9: 96 percent / PBr3, pyridine / benzene / 3 h 10: 91 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 11: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH4 / methanol / 0.2 h / 0 °C 7: 87 percent / PBr3, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 9: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h 10: 41 percent / BF3 / nitromethane / 2 h / -30 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH4 / methanol / 0.2 h / 0 °C 7: 87 percent / PBr3, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 9: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h 10: 41 percent / BF3 / nitromethane / 2 h / -30 °C 12: 91 percent / m-CPBA / CH2Cl2 / 1 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH4 / methanol / 0.2 h / 0 °C 7: 87 percent / PBr3, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 9: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h 10: 41 percent / BF3 / nitromethane / 2 h / -30 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 13 steps 1: 94 percent / diethyl ether / 0.17 h / Heating 2: 98 percent / glacial HOAc / 2 h / Heating 3: 97 percent / H2 / 5percent Pd/C / diethyl ether / 19 h / 2068.6 Torr 4: KBr, 18-crown-6, m-CPBA / CH2Cl2 / 0.5 h / 0 °C 5: 1) Mg / 1) THF, 2) cooling, then reflux, 5 min 6: NaBH4 / methanol / 0.2 h / 0 °C 7: 87 percent / PBr3, pyridine / benzene / 3 h 8: 77 percent / 18-crown-6 / acetonitrile / 1 h / 60 °C 9: 1) LDA / 1) THF, hexane, -78 deg C, 5 min, 2) -78 deg C -> rt, 3 h 10: 41 percent / BF3 / nitromethane / 2 h / -30 °C 12: 91 percent / m-CPBA / CH2Cl2 / 1 h / -78 °C 13: 82 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 35 percent / NaBH4, I2 / CHCl3 / 18 h 2: 58 percent / H2SO4 (d = 1.84) / 100 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 35 percent / NaBH4, I2 / CHCl3 / 18 h 2: 58 percent / H2SO4 (d = 1.84) / 100 h / Heating 3: 100 percent / K2CO3 / acetone / 8 h / Heating 4: 73 percent / NaOMe / benzene / 6 h / 10 °C 5: 100 percent / K2CO3 / acetone / 6 h / Heating 6: 90 percent / 0.25N aq. Na2CO3 / 1 h / Heating 7: 94 percent / Cu, pyridine / bis-(2-hydroxy-ethyl) ether / 0.33 h / 160 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 35 percent / NaBH4, I2 / CHCl3 / 18 h 2: 58 percent / H2SO4 (d = 1.84) / 100 h / Heating 3: 100 percent / K2CO3 / acetone / 8 h / Heating 4: 73 percent / NaOMe / benzene / 6 h / 10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile | 1 Preparation of Methyl 2,6-dimethoxybenzoate EXAMPLE 1 Preparation of Methyl 2,6-dimethoxybenzoate A solution containing 2,6-dimethoxybenzoic acid (5.0 g, 27.5 mmol), DBU (4.2 g, 27.5 mmol), DMC (50 mL), and acetonitrile (50 mL) was circulated at 20 mL/min by a pump through a Milestone ETHOS-CFR continuous-flow reactor, which had been preheated to 160° C. at 20 bar by microwave irradiation. The reaction mixture was analyzed by HPLC after each cycle (6 minutes microwave irradiation). The yield of methyl 2,6-dimethoxybenzoate after two cycles (12 minutes microwave irradiation time) as determined by HPLC was 99% conversion. The reaction mixture was concentrated under vacuum. The residue was diluted with EtOAc (100 mL) and H2O (80 mL). | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile | 1 Preparation of methyl 2,6-dimethoxybenzoate EXAMPLE 1 Preparation of methyl 2,6-dimethoxybenzoate A solution containing 2,6-dimethoxybenzoic acid (5.0 g, 27.5 mmol), DBU (4.2 g, 27.5 mmol), DMC (50 mL), and acetonitrile (50 mL) was circulated at 20 mL/min by a pump through a Milestone ETHOS-CFR continuous-flow reactor, which had been preheated to 160° C. at 20 bar by microwave irradiation. The reaction mixture was analyzed by HPLC after each cycle (6 minutes microwave irradiation). The yield of methyl 2,6-dimethoxybenzoate after two cycles (12 minutes microwave irradiation time) as determined by HPLC was 99% conversion. The reaction mixture was concentrated under vacuum. The residue was diluted with EtOAc (100 mL) and H2O (80 mL). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In dimethyl carbonate (DMC); water | 1 Preparation of methyl 2,6-dimethoxybenzoate using DBU catalyst EXAMPLE 1 Preparation of methyl 2,6-dimethoxybenzoate using DBU catalyst 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), (836 mg, 5.49 mmol), was added to a mixture of 2,6-dimethoxybenzoic acid (1), (1.0 g, 5.49 mmol), in dimethyl carbonate (DMC) (10 mL) and the resulting mixture was heated to reflux at 90° C. for 4 hours. The reaction mixture was cooled to 25° C. and diluted with EtOAc (30 mL) and water (30 mL). The organic layer was separated and washed in sequence with 10 mL of water, 2 M HCl (2*30 mL), saturated aqueous NaHCO3 (2*30 mL) and water (2*25 mL). The organic layer was dried over Na2SO4, filtered and concentrated under vacuum to give methyl 2,6-dimethoxybenzoate (2) as a white solid. The yield of the 2,6-dimethoxybenzoate as determined by HPLC was 97-98% conversion. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With lithium hexamethyldisilazane In tetrahydrofuran Cooling with ice; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 58% 2: 7% | With palladium diacetate; triphenylphosphine; p-benzoquinone at 20℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: methyl iodide With magnesium In diethyl ether at 20℃; for 1h; Stage #2: methyl 2,6-dimethoxybenzoate In tetrahydrofuran; diethyl ether for 2h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 13% 2: 63% | Stage #1: 1,3-Dimethoxybenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Stage #3: methanol Further stages; | 4.3. Typical procedure for one-pot conversion of aromatic bromides into aromatic methyl esters with DMF General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3×20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82% yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With copper quinolate In water; dimethyl sulfoxide at 120℃; for 24h; | |
84% | With copper doped mesoporous polymelamine-formaldehyde In water; dimethyl sulfoxide at 100℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium; ammonia / tetrahydrofuran; <i>tert</i>-butyl alcohol / Inert atmosphere; Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium; ammonia / tetrahydrofuran; <i>tert</i>-butyl alcohol / Inert atmosphere; Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 20 °C / Inert atmosphere 3: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; N,N-dimethyl-formamide / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dipotassium peroxodisulfate; copper(II) acetate monohydrate In acetic acid at 90℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique; Overall yield = 49 %; Overall yield = 32.4 mg; | ||
With dipotassium peroxodisulfate; copper(II) acetate monohydrate; acetic acid at 90℃; for 24h; Inert atmosphere; Sealed tube; Overall yield = 49 %; Overall yield = 32.4 mg; | 4 Methyl 2,6-dimethoxy-3-(trifluoromethyl)benzoate (10a) and methyl 2,6-dimethoxy-4- (trifluoromethyl)benzoate (10b) [00229] Methyl 2,6-dimethoxybenzoate (49.0 mg, 0.250 mmol, 1.00 eq), K2S208 (270 mg, 1.00 mmol, 4.00 eq) and Cu(OAc)2 FontWeight="Bold" FontSize="10" H20 (100 mg, 0.0500 mmol, 0.200 eq) were dissolved in glacial acetic acid (2.00 mL). TMG FontWeight="Bold" FontSize="10" CF3I (0.100 mL, 0.500 mmol, 2.00 eq) was added, the reaction vessel was sealed and heated at 90 °C for 24 hours. The reaction mixture was diluted with saturated aqueous sodium carbonate (50 mL) and the resulting mixture extracted with ethyl acetate (3 x 25 mL). The combined ethyl acetate extracts were dried (MgS04) and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with CH2Cl2/hexanes (1:2 to 1: 1) to afford 32.4 mg (0.123 mmol, 49%) of a mixture of 10a and 10b in a 3.0: 1 ratio. Further purification by preparative TLC (EtOAc/hexanes 1:4) afforded pure 10a as a colorless oil and 10b as a colorless solid, in quantities sufficient for characterization. [00230] Methyl 2,6-dimethoxy-3-(trifluoromethyl)benzoate (10a):R/= 0.22 (EtOAc/hexanes 1:4). NMR spectroscopy: 1H NMR (400 MHz, CDC13, 23 °C) δ ppm 7.58 (d, J = 8.8 Hz, 1H), 6.71 (d, J = 8.8 Hz, 1H), 3.95 (s, 3H), 3.89 (s, 3H), 3.87 (s, 3H). 13C NMR (125 MHz, CDC13, 23 °C) δ ppm 165.8, 160.2, 156.7, 129.3, 123.4 (q, JCF = 272 Hz), 119.2, 116.7 (q, JCF = 31 Hz), 105.9, 63.4, 56.3, 52.8. 19F NMR (376 MHz, CDC13, 23 °C) δ ppm -60.5. Mass spectrometry: HRMS (APCI) (m/z): Calcd for [CuHi2F304]+, [M+H+]: 265.0682. Found, 265.0674. [00231] Methyl 2,6-dimethoxy-4-(trifluoromethyl)benzoate (10b): R/= 0.30 (EtOAc/hexanes 1:4). NMR spectroscopy: 1H NMR (400 MHz, CDC13, 23 °C) δ ppm, 6.79 (s, 2H), 3.92 (s, 3H), 3.87 (s, 6H). 13C NMR (125 MHz, CDC13, 23 °C) δ ppm 165.8, 157.5, 133.2 (q, JcF = 33 Hz), 123.5 (q, JCF = 273 Hz), 115.9, 101.1, 56.3, 52.6. 19F NMR (376 MHz, CDC13, 23 °C) δ ppm -63.1. Mass spectrometry: HRMS (APCI) (m/z): Calcd for [CuHnF304Na]+, [M+]: 287.0502. Found, 287.0483. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With air at 20℃; for 36h; chemoselective reaction; | |
61% | With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]; trifluoroacetic acid In 2,2,2-trifluoroethanol at 0℃; for 2.5h; regioselective reaction; | |
61% | With Rh2(esp)2 In 2,2,2-trifluoroethanol at 0℃; for 2.5h; Inert atmosphere; | 4 FIG. 2: Entry 15 Following the general intermolecular amination procedure, methyl 2,6-dimethoxybenzoate (7s: 29 mg, 0.15 mmol), Du Bois' catalyst (2.3 mg, 3.0 μmol), and 32 TsONHMe (45 mg, 0.225 mmol) were stirred at 0° C. in TFE (2 mL) for 2.5 h. Chromatographic purification of the crude product afforded 92 methyl 2,6-dimethoxy-3-(methylamino)benzoate (8s: 20 mg, 61%) as a solid, mp 83.6° C. TLC: Rf≈0.5 (30% EtOAc/hexanes); 1H NMR (400 MHz, CDCl3) δ 6.65-6.58 (m, 2H), 3.92 (s, 3H), 3.77 (s, 3H), 3.75 (s, 3H), 2.81 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 167.01, 148.08, 144.54, 137.11, 118.19, 111.84, 107.79, 60.92, 56.61, 52.43, 30.97. HRMS (ESI+) Calcd. for [C11H15NO4+H]+ 226.1079, Found 226.1074. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With hydroxylamine hydrochloride; potassium hydroxide In methanol at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With sodium persulfate; phosphoric acid In water; acetonitrile at 30℃; for 72h; Sealed tube; Inert atmosphere; Green chemistry; Overall yield = 64 %; | |
With ammonium nitrate at 100℃; for 12h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 85℃; for 2h; Electrolysis; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol at 25℃; for 4h; Electrolysis; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,5-cyclooctadiene)(methoxy)iridium(l) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In tetrahydrofuran at 65℃; Inert atmosphere; Reflux; | 2.13 Int 14: mixture of methyl 2,6-dimethoxy-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzoate / (3,5-dimethoxy-4-methoxycarbonyl-phenyl)boronic acid Methyl 2,6-dimethoxybenzoate (CAS 2065-27-2; 96.6 g, 492 mmol, leq.), Ekpim (312.6 g, 1.23 mol, 2.5 eq.), [Ir(OMe)(COD)]2 (6.5 g, 9.8 mmol, 0.02 eq.) and 3,4,7,8-tetramethyl-l,l0-phenanthroline (Activate Scientific, Cat AS21433; 4.7 g, 20 mmol, 0.04 eq.) are dissolved in THF (1 L). The mixture is degassed with nitrogen and then heated to reflux. The reaction mixture is left to stir at 65 °C overnight. The solvent is concentrated in vacuo and the residue is triturated in diisopropyl ether (400 mL). The solid obtained is dried in a vacuum oven at 40 °C overnight to afford the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: bis(2-bromo-5-(dimethylamino)phenyl)(phenyl)phosphine oxide With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Inert atmosphere; Stage #2: methyl 2,6-dimethoxybenzoate In tetrahydrofuran; pentane at -78 - 20℃; for 2.5h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water; pentane at 20℃; for 0.25h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | Stage #1: (2-bromo-5-(dimethylamino)phenyl)(2-bromo-5-(pyrrolidin-1-yl)phenyl)(phenyl)phosphine oxide With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Inert atmosphere; Stage #2: methyl 2,6-dimethoxybenzoate In tetrahydrofuran; pentane at -78 - 25℃; for 2.5h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water; pentane at 25℃; for 0.25h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | Stage #1: bis(2-bromo-5-(dimethylamino)phenyl)(tert-butyl)phosphine oxide With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h; Inert atmosphere; Stage #2: methyl 2,6-dimethoxybenzoate In tetrahydrofuran; pentane at -20 - 20℃; for 7h; Inert atmosphere; Stage #3: acetic acid Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With bis(1,5-cyclooctadiene)nickel (0); 1,1,3,3-Tetramethyldisiloxane; potassium <i>tert</i>-butylate; 1,3-bis(cyclohexyl)imidazolium tetrafluoroborate In toluene at 110℃; for 12h; Glovebox; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With bis(1,5-cyclooctadiene)nickel (0); 1,1,3,3-Tetramethyldisiloxane; tricyclohexylphosphine In toluene at 110℃; for 12h; Glovebox; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere 2: thionyl chloride; pyridine / chloroform / 0.17 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere 2: thionyl chloride; pyridine / chloroform / 0.17 h / 20 °C / Inert atmosphere 3: N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere 2: thionyl chloride; pyridine / chloroform / 0.17 h / 20 °C / Inert atmosphere 3: acetonitrile / 7 h / 90 °C / Sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere 2: thionyl chloride; pyridine / chloroform / 0.17 h / 20 °C / Inert atmosphere 3: acetonitrile / 7 h / 90 °C / Sealed tube; Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / acetonitrile / 48 h / 115 °C / Sealed tube; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With perchloric acid; d(4)-methanol at 75℃; for 72h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84 %Spectr. | With CsPbBr3; N-ethyl-N,N-diisopropylamine; 1,1-dibromomethane Irradiation; |
Tags: 2065-27-2 synthesis path| 2065-27-2 SDS| 2065-27-2 COA| 2065-27-2 purity| 2065-27-2 application| 2065-27-2 NMR| 2065-27-2 COA| 2065-27-2 structure
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