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CAS No. : | 14963-97-4 | MDL No. : | MFCD17014918 |
Formula : | C9H8O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DULQZGQVLHMCAU-UHFFFAOYSA-N |
M.W : | 196.16 | Pubchem ID : | 315218 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 46.85 |
TPSA : | 83.83 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.59 cm/s |
Log Po/w (iLOGP) : | 0.88 |
Log Po/w (XLOGP3) : | 1.27 |
Log Po/w (WLOGP) : | 1.09 |
Log Po/w (MLOGP) : | 0.95 |
Log Po/w (SILICOS-IT) : | 0.65 |
Consensus Log Po/w : | 0.97 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.98 |
Solubility : | 2.08 mg/ml ; 0.0106 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.63 |
Solubility : | 0.46 mg/ml ; 0.00235 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.28 |
Solubility : | 10.4 mg/ml ; 0.0528 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.66 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 diethyl ether; ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.75% | With potassium permanganate; cetyltrimethylammonim bromide; In N,N-dimethyl-formamide; at 70 - 90℃; for 4.5h; | A 500 mL three-necked flask was charged with 100.00 g of DMF, 27.24 g (0.20 mol) of <strong>[2944-49-2]1-methoxy-2,3-dimethylbenzene</strong>,And cetyltrimethylammonium bromide 14.58g (0.04mol), warmed to 70 C, began to part-time potassium permanganate 79.01g (0.50mol), the temperature does not exceed 90 , about 30min plus finished,After adding insulation 80 ~ 90 reaction 4h,Cooled to room temperature, 300g of water was added dropwise, filtered and washed with water 100.00g * 3 to give a white solid, dried at 55-60 C, the theoretical 39.23g,Yield 76.75%, purity 98.70%. |
75% | With potassium permanganate; In tert-butyl alcohol; for 0.5h;Reflux; | 2) 2,3-Dimethyl anisole is dissolved in tert-butyl alcohol. Under reflux, potassium permanganate solution is added dropwise until dissolved.After the liquid color remains reddish for 30 minutes, add a little sodium sulfite to remove excess potassium permanganate, filter, and extract with ethyl acetate.Taken, the extract was distilled off to give 3-methoxyphthalic acid in a yield of 75%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With acetic anhydride In tetrahydrofuran at 80℃; for 3h; | 11 [0228] To a solution of 3-methoxyphthalic acid (3.0 g, 15.306 mmol) in THF (24 mL) at RT was added acetic anhydride (10 mL). The mixture was stirred at 80 oC for 3 hrs. The solvent was evaporated to give 4-methoxyisobenzofuran-1,3-dione (2.72 g, quant. yield) as a white solid. MS (ESI) m/z = 178.9 [M+H]+. |
99% | With acetic anhydride In tetrahydrofuran for 4h; Heating / reflux; | 56.56A Acetic anhydride (70 ml) was added to a mixture of 3-methoxyphthalic acid (51.0 g, 0.26 mol) in anhydrous tetrahydrofuran (250 ml) and the mixture was strirred and held at reflux for 4 hours. Upon cooling to room temperature the solvent was removed in vacuo and the resulting solid material was dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic anhydride (45.9 g, 99%) as a colourless solid. 1H NMR (DMSOd6) 7.97 (1 H, dd), 7.63 (1 H, d), 7.60 (1 H, d), 4.02 (3H, s). MS: [M+H]+ 179. |
99% | With acetic anhydride In tetrahydrofuran for 4h; Heating / reflux; | 56.A A suspension of dimethyl 3-methoxyphthalate (69.45 g, 0.31 mo.) [prepared as per J. Chem, Soc,Perkin Trans. 7, 1989, 391] in water (300 ml) was treated with potassium hydroxide (43.7 g, 0.78 mol) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol liberated during the course of the reaction was removed in vacuo, the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid and evaporated gently in vacuo to induce crystallization. The solid material was filtered off, washed with a little ice cooled water, sucked dry under reduced pressure and dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic acid (51.0 g, 84%) as a colourless solid. 1H NMR (DMSO-d6) 13.05 (2H, br s), 7.48 (2H, m), 7.33 (1H, m), 3.82 (3H, s). MS: [M+H]+ 197.Acetic anhydride (70 ml) was added to a mixture of 3-methoxyphthalic acid (51.0 g, 0.26 mol) in anhydrous tetrahydrofuran (250 ml) and the mixture was strirred and held at reflux for 4 hours. Upon cooling to room temperature the solvent was removed in vacuo and the resulting solid material was dried in a vacuum oven at 500C overnight to afford 3-methoxyphthalic anhydride (45.9 g, 99%) as a colourless solid. 1H NMR (DMSOd6) 7.97 (1 H, dd), 7.63 (1 H, d), 7.60 (1H, d), 4.02 (3H, s). MS: [M+H]+ 179.A mixture of 3-methoxyphthalic anhydride (24.0 g, 134.8 mmol) and formamide (120 ml) was stirred and held at 2100C for 5 hours and was then allowed to cool to room temperature overnight. Water (100 ml) was added and the solid material filtered off under reduced pressure. The crude product was washed sequentially with 50% aqueous acetone (50 ml) and diethyl ether (200 ml) and sucked dry under reduced pressure to afford 3-methoxyphthalimide (8.95 g, 37%) as an off-white solid. 1H NMR (DMSOd6) 11.08 (1 H, br s), 7.78 (1H, dd), 7.45 (1H, d), 7.36 (1 H1 d), 3.93 (3H, s). MS: [M+Hf 178.A stirred solution of 3-methoxyphthalimide (8.95 g, 50.56 mmol) in anhydrous tetrahydrofuran (200 ml) at O0C was treated dropwise with a solution of borane in tetrahydrofuran (1M, 150 ml, 0.15 mol) and the resulting mixture was stirred and held at reflux for 16 hours. The mixture was cooled to O0C, methanol (60 ml) was added dropwise followed by 5M hydrochloric acid (60 ml) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the mixture diluted with water (250 ml) and extracted with dichloromethane (3 x 250 ml). The aqueous layer was basified to pH 12 or above by the addition of 5M sodium hydroxide, extracted with dichloromethane (3 x 250 ml) and the combined extracts were evaporated to dryness in vacuo to afford 4-methoxyisoindoline (4.44 g, 59%) as a green oil which was used without further purification. 1H NMR (DMSO-d6) 7.18 (1H, t), 6.83 (1 H, d), 6.78 (1 H, d), 4.07 (2H1 s), 4.02 (2H, s), 3.78 (3H, s). MS: [M+H]+ 150.4-Methoxyisoindoline (4.4 g, 29.53 mmol) in 48% aqueous hydrobromic acid (50 ml) was stirred and held at reflux for 16 hours. Upon cooling to room temperature the solvent was removed in vacuo to afford 4-hydroxyisoindoline hydrobromide (5.0 g, 78%) as a pale orange solid. 1H NMR (DMSO-d6) 9.95 (1 H, br s), 9.37 (2H, br s), 7.19 (1 H, t), 6.84 (1 H, d), 6.80 (1H, d), 4.48 (2H, t), 4.40 (2H, t). MS: [M+Hf 136. |
99% | With acetic anhydride In tetrahydrofuran for 4h; Heating / reflux; | 56.A Acetic anhydride (70 ml) was added to a mixture of 3-methoxyphthalic acid (51.0 g, 0.26 mol) in anhydrous tetrahydrofuran (250 ml) and the mixture was strirred and held at reflux for 4 hours. Upon cooling to room temperature the solvent was removed in vacuo and the resulting solid material was dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic anhydride (45.9 g, 99%) as a colourless solid. 1H NMR (DMSO-d6) 7.97 (1 H, dd), 7.63 (1H1 d), 7.60 (1 H1 d), 4.02 (3H, s). MS: [M+H]+ 179. |
99% | With acetic anhydride In tetrahydrofuran for 4h; Reflux; | 56.A 56A. Acetic anhydride (70 ml) was added to a mixture of 3-methoxyphthalic acid (51.0 g, 0.26 mol) in anhydrous tetrahydrofuran (250 ml) and the mixture was stirred and held at reflux for 4 hours.Upon cooling to room temperature the solvent was removed in vacuo and the resulting solid material was dried in a vacuum oven at 50° C. overnight to afford 3-methoxyphthalic anhydride (45.9 g, 99%) as a colourless solid. 1H NMR (DMSO-d6) 7.97 (1H, dd), 7.63 (1H, d), 7.60 (1H, d), 4.02 (3H, s). MS: [M+H]+ 179. |
97.8% | With acetic anhydride In tetrahydrofuran at 20 - 80℃; for 4h; | (S)-2-((2-(2,7-Dioxoazepan-3-yl)- 1 ,3-dioxoisoindolin-4-yl)oxy)-N-(6-(2-((1 -(4-(3-oxo-9- phenyl-2,3 -dihydro- [1 ,2,4ltriazolo[3 ,4-fl [1 ,6lnaphthyridin-8-yl)phenyl)cyclobutyl)amino)acetamido)hexyl)acetamide (Compound 73) [0582] To a solution of 3-methoxyphthalic acid (3.0 g, 15.3 mmol) in THF (30 mL) at rt was added acetic anhydride (10 mL) and the reaction was heated at 80°C for 4 hrs. The solvent was removed and the residue was dried under vacuum providing 4- methoxyisobenzofuran-1,3-dione (2.66 g, 97.8% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.98-7.94 (m, 1H), 7.63-7.59 (m, 2H), 4.01 (s, 3H). |
95% | at 200℃; | |
94% | With acetic anhydride Reflux; | 1.3 3) 3-methoxy-phthalic acid plus 2 times the weight of acetic anhydride, after heating and refluxing, cooling and crystallization,The 3-methoxy-phthalic anhydride is filtered,Yield 94%. |
at 170℃; Erhitzen unter vermindertem Druck; | ||
With acetic anhydride; acetyl chloride | ||
With acetic anhydride | ||
With acetic anhydride for 1h; Heating; | ||
With acetic anhydride Heating; | ||
With acetyl chloride for 6h; Yield given; | ||
Multi-step reaction with 2 steps 1: 65 percent / Amberlyst 15 beads / 48 h / Heating 2: thionyl chloride / 2 h / 20 °C | ||
With acetic anhydride In tetrahydrofuran for 4h; Reflux; | 3.1.1. General Procedure for Synthesis of 4-Methoxy-2-benzofuran-1,3-dione (2) The 4-methoxy-2-benzofuran-1,3-dione was obtained from1, according to a previously published procedure [32], with slight modifications. Briefly, 2,3-dimethylphenyl methyl ether (3.4 g, 25 mmol) was dissolved in water (98 mL) and tert-butanol (42 mL). After potassium permanganate (25 g, 160 mmol) was added, the reaction mixture was refluxed for 12 h. The resulting suspension was filtered over Celite, concentrated to 50 mL, acidified with 37% hydrochloric acid, and left standing overnight at room temperature. The 3-methoxybenzene-1,2-dicarboxylic acid crystallized as a white solid (4.34 g) and was refluxed for 4 h in anhydrous tetrahydrofuran (24 mL) with the addition of acetic anhydride (7 mL). Upon cooling to room temperature, the reaction mixture was concentrated in vacuo and the white solid was dried at 50 °C for 48 h, to afford 4-methoxy-2-benzofuran-1,3-dione (3.82, 97%). HPLC:Rt= 0.931, MS calcd for [M + H]+: C9H6O4m/z: 178.14, found: 178.97;1H-NMR (300 MHz, DMSO-d6) δ ppm 3.99 (s, 3 H) 7.59 (dd,J= 9.67, 7.91 Hz, 2 H) 7.90-7.97 (m, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.98% | With boron tribromide In dichloromethane at 10 - 15℃; for 5h; | 6 A 500 mL three-necked flask was charged with 150.00 g of methylene chloride and 30.00 g of 3-methoxyphthalic acid(0.15mol), water bath temperature 10 ~ 15 ° C was added dropwise boron tribromide 95.22g (0.38mol), after the addition was completed, the reaction was continued heat5h. In another 1000mL three-necked flask was added 450.00g ice water mixture, the above reaction solution was slowly poured into ice water, controlTemperature does not exceed 30 ° C, and then continue stirring for 1h, filtered, washed with water to pH = 6, 55 ~ 60 dried to give a white solid, theory27.79g,Real 25.56g, yield 91.98%, purity 99.23%. |
With potassium carbonate beim Schmelzen; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With potassium hydroxide In ethanol; water | |
99% | With potassium hydroxide In ethanol; water other reagents and solvents at various temperatures; | |
84% | Stage #1: dimethyl 3-methoxyphthalate With potassium hydroxide; water for 4h; Heating / reflux; Stage #2: With hydrogenchloride In water | 56.56A A suspension of dimethyl 3-methoxyphthalate (69.45 g, 0.31 mol) [prepared as per J. Chem. Soc,Perkin Trans. 1, 1989, 391] in water (300 ml) was treated with potassium hydroxide (43.7 g, 0.78 mol) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol liberated during the course of the reaction was removed in vacuo, the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid and evaporated gently in vacuo to induce crystallization. The solid material was filtered off, washed with a little ice cooled water, sucked dry under reduced pressure and dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic acid (51.0 g, 84%) as a colourless solid. 1H NMR (DMSOd6) 13.05 (2H1 br s), 7.48 (2H, m), 7.33 (1 H, m), 3.82 (3H, s). MS: [M+H]+ 197. |
84% | Stage #1: dimethyl 3-methoxyphthalate With potassium hydroxide; water for 4h; Heating / reflux; Stage #2: With hydrogenchloride In water | 56.A A suspension of dimethyl 3-methoxyphthalate (69.45 g, 0.31 mo.) [prepared as per J. Chem, Soc,Perkin Trans. 7, 1989, 391] in water (300 ml) was treated with potassium hydroxide (43.7 g, 0.78 mol) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol liberated during the course of the reaction was removed in vacuo, the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid and evaporated gently in vacuo to induce crystallization. The solid material was filtered off, washed with a little ice cooled water, sucked dry under reduced pressure and dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic acid (51.0 g, 84%) as a colourless solid. 1H NMR (DMSO-d6) 13.05 (2H, br s), 7.48 (2H, m), 7.33 (1H, m), 3.82 (3H, s). MS: [M+H]+ 197.Acetic anhydride (70 ml) was added to a mixture of 3-methoxyphthalic acid (51.0 g, 0.26 mol) in anhydrous tetrahydrofuran (250 ml) and the mixture was strirred and held at reflux for 4 hours. Upon cooling to room temperature the solvent was removed in vacuo and the resulting solid material was dried in a vacuum oven at 500C overnight to afford 3-methoxyphthalic anhydride (45.9 g, 99%) as a colourless solid. 1H NMR (DMSOd6) 7.97 (1 H, dd), 7.63 (1 H, d), 7.60 (1H, d), 4.02 (3H, s). MS: [M+H]+ 179.A mixture of 3-methoxyphthalic anhydride (24.0 g, 134.8 mmol) and formamide (120 ml) was stirred and held at 2100C for 5 hours and was then allowed to cool to room temperature overnight. Water (100 ml) was added and the solid material filtered off under reduced pressure. The crude product was washed sequentially with 50% aqueous acetone (50 ml) and diethyl ether (200 ml) and sucked dry under reduced pressure to afford 3-methoxyphthalimide (8.95 g, 37%) as an off-white solid. 1H NMR (DMSOd6) 11.08 (1 H, br s), 7.78 (1H, dd), 7.45 (1H, d), 7.36 (1 H1 d), 3.93 (3H, s). MS: [M+Hf 178.A stirred solution of 3-methoxyphthalimide (8.95 g, 50.56 mmol) in anhydrous tetrahydrofuran (200 ml) at O0C was treated dropwise with a solution of borane in tetrahydrofuran (1M, 150 ml, 0.15 mol) and the resulting mixture was stirred and held at reflux for 16 hours. The mixture was cooled to O0C, methanol (60 ml) was added dropwise followed by 5M hydrochloric acid (60 ml) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the mixture diluted with water (250 ml) and extracted with dichloromethane (3 x 250 ml). The aqueous layer was basified to pH 12 or above by the addition of 5M sodium hydroxide, extracted with dichloromethane (3 x 250 ml) and the combined extracts were evaporated to dryness in vacuo to afford 4-methoxyisoindoline (4.44 g, 59%) as a green oil which was used without further purification. 1H NMR (DMSO-d6) 7.18 (1H, t), 6.83 (1 H, d), 6.78 (1 H, d), 4.07 (2H1 s), 4.02 (2H, s), 3.78 (3H, s). MS: [M+H]+ 150.4-Methoxyisoindoline (4.4 g, 29.53 mmol) in 48% aqueous hydrobromic acid (50 ml) was stirred and held at reflux for 16 hours. Upon cooling to room temperature the solvent was removed in vacuo to afford 4-hydroxyisoindoline hydrobromide (5.0 g, 78%) as a pale orange solid. 1H NMR (DMSO-d6) 9.95 (1 H, br s), 9.37 (2H, br s), 7.19 (1 H, t), 6.84 (1 H, d), 6.80 (1H, d), 4.48 (2H, t), 4.40 (2H, t). MS: [M+Hf 136. |
84% | Stage #1: dimethyl 3-methoxyphthalate With potassium hydroxide; water for 4h; Heating / reflux; Stage #2: With hydrogenchloride In water | 56.A A suspension of dimethyl 3-methoxyphthalate (69.45 g, 0.31 mol) [prepared as per J. Chem. Soc,Perkin Trans. 1, 1989, 391] in water (300 ml) was treated with potassium hydroxide (43.7 g, 0.78 mol) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol liberated during the course of the reaction was removed in vacuo, the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid and evaporated gently in vacuo to induce crystallization. The solid material was filtered off, washed with a little ice cooled water, sucked dry under reduced pressure and dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic acid (51.0 g, 84%) as a colourless solid. 1H NMR (DMSOd6) 13.05 (2H, br s), 7.48 (2H, m), 7.33 (1H, m), 3.82 (3H, s). MS: [M+H]+ 197. |
84% | Stage #1: dimethyl 3-methoxyphthalate With potassium hydroxide; water for 4h; Heating / reflux; Stage #2: With hydrogenchloride In water | 56.56A A suspension of dimethyl 3-methoxyphthalate (69.45 g, 0.31 mol) [prepared as per J. Chem. Soc, Perkin Trans. 1, 1989, 391] in water (300 ml) was treated with potassium hydroxide (43.7 g, 0.78 mol) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol liberated during the course of the reaction was removed in vacuo, the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid and evaporated gently in vacuo to induce crystallization. The solid material was filtered off, washed with a little ice cooled water, sucked dry under reduced pressure and dried in a vacuum oven at 5O0C overnight to afford 3-methoxyphthalic acid (51.0 g, 84%) as a colourless solid. 1H NMR (DMSO-d6) 13.05 (2H, br s), 7.48 (2H, m), 7.33 (1H, m), 3.82 (3H, s). MS: [M+Hf 197. |
84% | With water; potassium hydroxide for 4h; Reflux; | 56.A 56A. A suspension of dimethyl 3-methoxyphthalate (69.45 g, 0.31 mol) [prepared as per J. Chem. Soc., Perkin Trans. 1, 1989, 391] in water (300 ml) was treated with potassium hydroxide (43.7 g, 0.78 mol) and the mixture was stirred and held at reflux for 4 hours. Upon cooling to room temperature the methanol liberated during the course of the reaction was removed in vacuo, the mixture acidified to pH 2 or below by the addition of 5M hydrochloric acid and evaporated gently in vacuo to induce crystallization. The solid material was filtered off, washed with a little ice cooled water, sucked dry under reduced pressure and dried in a vacuum oven at 50° C. overnight to afford 3-methoxyphthalic acid (51.0 g, 84%) as a colourless solid. 1H NMR (DMSO-d6) 13.05 (2H, br s), 7.48 (2H, m), 7.33 (1H, m), 3.82 (3H, s). MS: [M+H]+ 197. |
Hydrolysis; | ||
hydrolysis; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium permanganate; sulfuric acid at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With Amberlyst 15 beads for 48h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium hydroxide; potassium permanganate In water for 12h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.55% | With potassium permanganate; cetyltrimethylammonim bromide In dimethyl sulfoxide at 75 - 90℃; for 3.16667h; | 3 To a 1000 mL three-necked flask, 120.0 g of DMSO, 32.45 g of 5-methoxy-1,2,3,4-tetrahydronaphthalene(0.20 mol) and cetyltrimethylammonium bromide 36.44g (0.10mol), warmed to 75 ° C, the beginning of the partial addition of permanganic acidPotassium 110.62g (0.70mol), temperature control does not exceed 90 , about 40min plus finished, after adding insulation 80 ~ 90 reaction 2.5h, coolingTo room temperature, dropping 600g of water, filtration, water 100.00g * 3 washed, to give a white solid, 55 ~ 60 drying theory 39.23g,Real 28.07g, yield 71.55%, purity 98.41%. |
65% | With potassium permanganate; cetyltrimethylammonim bromide In water; benzene for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 2h; Heating; | |
20% | Stage #1: 3-methoxyphthalic acid With dimethylsulfide borane complex In tetrahydrofuran at -6 - 55℃; Stage #2: With sodium hydroxide In tetrahydrofuran at 20℃; for 1h; | |
With sodium hydroxide In tetrahydrofuran; water | 5 EXAMPLE 5 EXAMPLE 5 A solution of 3-methoxyphthalic acid (19.6 g, 0.1 mol) in 100 ml of tetrahydrofuran was added to 10 g (0.263 mol) of lithium aluminum hydride in 500 ml of anhydrous ether at a rate sufficient to maintain a constant reflux. The mixture was refluxed for 2 hours after the addition was completed. It was cooled and decomposed by the addition of 10 ml of water, 20 ml of 10% sodium hydroxide and 40 ml of water. The resulting solid was separated by filtration and washed with tetrahydrofuran. The combined filtrates were concentrated to give 12 g of 3-methoxy-o-xylene-α,α'-diol; m.p. 95°. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; potassium permanganate In water Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sodium hydroxide In ethanol; water for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | at 170℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With potassium permanganate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With hydroxylamine hydrochloride at 170℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 74 percent / tetabutylammonium hydrogensulfate; K2CO3 / acetone / 24 h / Heating 2: 40 percent / KMnO4 / 2-methyl-propan-2-ol; H2O / 2 h / Heating | ||
Multi-step reaction with 2 steps 1: NaOH-solution 2: potassium permanganate | ||
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 2 h / 10 - 50 °C 2: potassium permanganate / <i>tert</i>-butyl alcohol / 0.5 h / Reflux |
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 75 °C 2: potassium permanganate / water; <i>tert</i>-butyl alcohol / 12 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: borane-methyl sulfide complex / tetrahydrofuran / -6 - 55 °C 1.2: 20 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / PBr3 / diethyl ether / 9 h / Heating 3.1: 13 percent / tetrabutylammonium bromide; sodium hydroxide / toluene / 5.83 h / 14 - 18 °C 4.1: 60 percent / sodium hydroxide; water / ethanol / Heating 5.1: 58 percent / triethylamine; diphenylphosphoryl azide / toluene / 8 h / Heating 6.1: BBr3 / CH2Cl2 / 0 °C 7.1: aq. hydrochloric acid / 20 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: borane-methyl sulfide complex / tetrahydrofuran / -6 - 55 °C 1.2: 20 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / PBr3 / diethyl ether / 9 h / Heating 3.1: 13 percent / tetrabutylammonium bromide; sodium hydroxide / toluene / 5.83 h / 14 - 18 °C 4.1: 60 percent / sodium hydroxide; water / ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: borane-methyl sulfide complex / tetrahydrofuran / -6 - 55 °C 1.2: 20 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / PBr3 / diethyl ether / 9 h / Heating 3.1: 13 percent / tetrabutylammonium bromide; sodium hydroxide / toluene / 5.83 h / 14 - 18 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: borane-methyl sulfide complex / tetrahydrofuran / -6 - 55 °C 1.2: 20 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / PBr3 / diethyl ether / 9 h / Heating 3.1: 13 percent / tetrabutylammonium bromide; sodium hydroxide / toluene / 5.83 h / 14 - 18 °C 4.1: 60 percent / sodium hydroxide; water / ethanol / Heating 5.1: 58 percent / triethylamine; diphenylphosphoryl azide / toluene / 8 h / Heating 6.1: BBr3 / CH2Cl2 / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: borane-methyl sulfide complex / tetrahydrofuran / -6 - 55 °C 1.2: 20 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / PBr3 / diethyl ether / 9 h / Heating 3.1: 13 percent / tetrabutylammonium bromide; sodium hydroxide / toluene / 5.83 h / 14 - 18 °C 4.1: 60 percent / sodium hydroxide; water / ethanol / Heating 5.1: 58 percent / triethylamine; diphenylphosphoryl azide / toluene / 8 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: borane-methyl sulfide complex / tetrahydrofuran / -6 - 55 °C 1.2: 20 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / PBr3 / diethyl ether / 9 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / Heating 2: L-Selectride / tetrahydrofuran / 2 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: acetic anhydride / 1 h / Heating 2: LiBH4 / tetrahydrofuran / 2 h / -10 - 20 °C / other 3-substituted phthalic anhydrides; var. reducing agents and reaction conditions | ||
Multi-step reaction with 2 steps 1: 170 °C / Erhitzen unter vermindertem Druck 2: acetic acid; aqueous hydrochloric acid; zinc |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / Heating 2: L-Selectride / tetrahydrofuran / 2 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: acetic anhydride / 1 h / Heating 2: LiBH4 / tetrahydrofuran / 2 h / -10 - 20 °C / other 3-substituted phthalic anhydrides; var. reducing agents and reaction conditions | ||
Multi-step reaction with 2 steps 1: 170 °C / Erhitzen unter vermindertem Druck 2: acetic acid; aqueous hydrochloric acid; zinc |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C 4: 79 percent / Ni(Ra), H2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C 4: 79 percent / Ni(Ra), H2 5: 69 percent / 48percent aq. HBr / Heating 6: 0.7 g / pyridine / 1 h / Ambient temperature 7: 0.4 g / 10percent aq. NaOH / ethanol / 0.5 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C 4: 79 percent / Ni(Ra), H2 5: 69 percent / 48percent aq. HBr / Heating 6: 0.7 g / pyridine / 1 h / Ambient temperature 7: 0.4 g / 10percent aq. NaOH / ethanol / 0.5 h / 50 °C 8: 0.4 g / K2CO3 / acetone / 8 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C 4: 79 percent / Ni(Ra), H2 5: 69 percent / 48percent aq. HBr / Heating 6: 0.7 g / pyridine / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C 4: 79 percent / Ni(Ra), H2 5: 69 percent / 48percent aq. HBr / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C 4: 79 percent / Ni(Ra), H2 5: 69 percent / 48percent aq. HBr / Heating 6: 0.7 g / pyridine / 1 h / Ambient temperature 7: 0.4 g / 10percent aq. NaOH / ethanol / 0.5 h / 50 °C 8: 0.4 g / K2CO3 / acetone / 8 h / Heating 9: LiAlH4 / diethyl ether / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 70 percent / 1 h / 170 °C 2: hydrochloric acid / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 95 percent / Raney-nickel / ethanol / 150 °C / 91200.1 - 114000 Torr 2: 65 percent / KMnO4 / cetyltrimethylammonium bromide / benzene; H2O / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: H3BO3 / 6 h / Heating 2: Ag2O / dimethylformamide 3: KMnO4, KOH / H2O / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: K2CO3 / acetone / 12 h / Heating 2: KMnO4, KOH / H2O / Heating | ||
Multi-step reaction with 2 steps 1: Ag2O / dimethylformamide 2: KMnO4, KOH / H2O / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Ag2O / dimethylformamide 2: KMnO4, KOH / H2O / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 65 mg / HCl(aq.) / methanol; H2O / 3 h / Heating 2: KMnO4, KOH / H2O / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 65 percent / Amberlyst 15 beads / 48 h / Heating 2: thionyl chloride / 2 h / 20 °C 3: 30 percent / AlCl3 / nitrobenzene / 18 h / 20 °C 4: 343 mg / triethylsilane / trifluoroacetic acid / 18 h | ||
Multi-step reaction with 3 steps 1: 65 percent / Amberlyst 15 beads / 48 h / Heating 2: 1.) thionyl chloride, 2.) stannic chloride, 3.) 10percent aq. KOH 3: 343 mg / triethylsilane / trifluoroacetic acid / 18 h | ||
Multi-step reaction with 3 steps 1: 95 percent / 200 °C 2: 30 percent / AlCl3 / nitrobenzene / 18 h / 20 °C 3: 343 mg / triethylsilane / trifluoroacetic acid / 18 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 65 percent / Amberlyst 15 beads / 48 h / Heating 2: thionyl chloride / 2 h / 20 °C 3: 30 percent / AlCl3 / nitrobenzene / 18 h / 20 °C | ||
Multi-step reaction with 2 steps 1: 65 percent / Amberlyst 15 beads / 48 h / Heating 2: 1.) thionyl chloride, 2.) stannic chloride, 3.) 10percent aq. KOH | ||
Multi-step reaction with 2 steps 1: 95 percent / 200 °C 2: 30 percent / AlCl3 / nitrobenzene / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potash / beim Schmelzen 2: 150 °C | ||
Multi-step reaction with 2 steps 1: boron tribromide / dichloromethane / 5 h / 10 - 15 °C 2: dicyclohexyl-carbodiimide / dimethyl sulfoxide / 1 h / 150 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetonitrile 2: NaNH2, liq. NH3 3: aq. NaOH, KMnO4 4: aq. NaOH, KMnO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: K2CO3 / acetone 2: KMnO4, aq. NaOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With hydrogenchloride In methanol; water-methanol | 6 Preparation of Methoxyphthalic Acid Monomethylester [derivative of formula (VIII) in which R2 =R3 =CH3 ] EXAMPLE 6 Preparation of Methoxyphthalic Acid Monomethylester [derivative of formula (VIII) in which R2 =R3 =CH3 ] A solution of methoxyphthalic acid obtained as per Example 5 (0.1 mol) in 100 ml methanol was added with CuCl (0.1 mol) and HCl (0.1 mol). The solution was heated to reflux for 30 min. The clear solution obtained was evaporated to dryness under reduced pressure. The residue obtained was dissolved in a 1:3 water-methanol mixture and acidified. The product was separated by cooling, collected by filtration and air dried. The product yield was 63-66%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In tetrahydrofuran for 4h; Heating / reflux; | 56.56A Acetic anhydride (70 ml) was added to a mixture of 3-methoxyphthalic acid (51.0 g, 0.26 mol) in anhydrous tetrahydrofuran (250 ml) and the mixture was strirred and held at reflux for 4 hours. Upon cooling to room temperature the solvent was removed in vacuo and the resulting solid material was dried in a vacuum oven at 500C overnight to afford 3-methoxyphthalic anhydride (45.9 g, 99%) as a colourless solid. 1H NMR (DMSO-d6) 7.97 (1 H, dd), 7.63 (1 H, d), 7.60 (1 H, d), 4.02 (3H, s). MS: [M+H]+ 179. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With sodium acetate; palladium diacetate; silver carbonate In 1,4-dioxane at 150℃; for 30h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-dimethylanisole With potassium permanganate In water; <i>tert</i>-butyl alcohol for 6h; Reflux; Stage #2: With hydrogenchloride In water; <i>tert</i>-butyl alcohol | 98-2 SYNTHESIS EXAMPLE 98-2 After 2,3-dimethyl anisole (10 g) was dissolved in a mixed solvent of water (250 mL) and t-butanol (112 mL), potassium permanganate (81.2 g) was added, and the mixture was heated to reflux for 6 hours. After cooling to room temperature, an insoluble matter was filtered with Celite, followed by washing with water. After the filtrate was acidified with concentrated hydrochloric acid and concentrated under reduced pressure, a mixture (4.9 g) of 3-methoxyphthalic anhydride and 3-methoxyphthalic acid was obtained. This mixture was heated to reflux in acetic anhydride (8.5 mL) for 2 hours. After an insoluble matter was filtered off in the hot state, the filtrate was left overnight at room temperature, and the precipitated crude crystal was washed with a t-butylmethylether/petroleum ether mixed solvent to obtain 3-methoxyphthalic anhydride (3.21 g). 1H-NMR (CDCl3, δ ppm): 4.08 (3H, s), 7.33 (1H, d), 7.58 (1H, d), 7.84 (1H, dd). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sulfuric acid / Reflux 2.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C 3.1: sodium hydroxide; water / 1,4-dioxane / 80 °C 3.2: pH 3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.9% | Stage #1: diethyl 3-methoxyphthalate With water; sodium hydroxide In 1,4-dioxane at 80℃; Stage #2: With hydrogenchloride In water | 4.2 3-Methoxyphthalic acid (5b) To a 1,4-dioxane (1.0 mL) solution of 4b (34.0 mg, 0.135 mmol), 5.0 mol/L NaOH solution (5.0 mL) was added. The mixture was stirred at 80°C for overnight. The reaction mixture was extracted with EtOAc three times. 1.0 mol/L HCl solution was added to the aqueous solution to adjust the until pH3, and then extracted with EtOAc three times. The organic layers were dried over anhydrous MgSO4 and concentrated under reduced pressure to give 5b (14.0 mg, 52.9%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.32% | With potassium permanganate; cetyltrimethylammonim bromide In water at 80 - 90℃; for 6.5h; | 2 To 500mL three-necked flask was added 240.00g of water,1-Methoxy-2-ethyl-3-methylbenzene 30.04 g (0.20 mol)And 7.29 g (0.02 mol) of cetyltrimethylammonium bromide were added, and the temperature was raised to 80 ° C and 63.21 g of potassium permanganate(0.40mol), temperature control does not exceed 90 , about 30min plus finished, after adding insulation 80 ~ 90 reaction 6h, cooled to room temperature, tooFiltered, washed with water 100.00g * 3, to give a white solid, dried at 55 ~ 60 , the theory of 39.23g, solid 32.17g, yield82.00%, purity of 98.32%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.8% | With potassium permanganate; cetyltrimethylammonim bromide In water at 70 - 90℃; for 8.5h; | 4 To 500mL of three-necked flask was added 250.00g of water,1-methoxy-2-propyl-335.65 g (0.20 mol) of ethylbenzene And 7.29 g (0.02 mol) of cetyltrimethylammonium bromide were added, and the temperature was raised to 70 ° C and 63.21 g of potassium permanganate(0.41mol), temperature control does not exceed 90 , about 30min plus finished, after adding insulation 80 ~ 90 reaction 8h, cooled to room temperature, tooFiltered, washed with water 100.00g * 3, to give a white solid, dried at 55 ~ 60 , the theory of 39.23g, was 31.70g, yield80.80%, purity of 98.03%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.98% | With potassium permanganate; cetyltrimethylammonim bromide; In water; at 70 - 90℃; for 7.5h; | To a 500 mL three-necked flask, 210.00 g of water and 29.64 g (0.20 mol) of <strong>[21573-42-2]<strong>[21573-42-2]4-methoxyindan</strong>e</strong> were added,And 7.29 g (0.02 mol) of cetyltrimethylammonium bromide were added, and the temperature was raised to 70 C. 79.02 g (0.50 mol) of potassium permanganate was added in portions,Temperature does not exceed 90 , about 30min plus finished, after adding insulation 80 ~ 90 reaction 7h, cooled to room temperature, filtered, water 100.00g * 3Washed to give a white solid, 55 ~ 60 drying theory 39.23g, in real 32.16g, yield 81.98%, purity 98.53%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77.57% | With potassium permanganate; cetyltrimethylammonim bromide In N,N-dimethyl-formamide at 70 - 90℃; for 4.5h; | 6 To a 500 mL three-necked flask were added 100.00 g of DMF, 38.46 g (0.2 mol) of 1-methoxy-2,3-dipropylbenzene andCetyltrimethylammonium bromide 14.58g (0.04mol), warmed to 70 ° C, the initial addition of potassium permanganate 79.01g(0.50mol), temperature control does not exceed 90 , about 30min plus finished, after adding insulation 80 ~ 90 reaction 4h, cooled to room temperature, dropwise300.00g of water, filtered, washed with water 100.00g * 3, to give a white solid, 55 ~ 60 drying,Theory 39.23g, in fact, 30.43g, yield 77.57%, purity 98.91%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C | ||
Multi-step reaction with 2 steps 1.1: acetic anhydride / tetrahydrofuran / 3 h / 80 °C 2.1: acetic acid / acetonitrile / 85 °C 2.2: 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C 4: boron tribromide / dichloromethane / 1 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C 4: boron tribromide / dichloromethane / 1 h / 0 - 20 °C 5: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C 4: boron tribromide / dichloromethane / 1 h / 0 - 20 °C 5: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 - 80 °C 6: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C 4: boron tribromide / dichloromethane / 1 h / 0 - 20 °C 5: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 - 80 °C 6: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C 7: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C 4: boron tribromide / dichloromethane / 1 h / 0 - 20 °C 5: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 - 80 °C 6: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C 7: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: acetic anhydride / tetrahydrofuran / 4 h / 20 - 80 °C 2: acetic acid / acetonitrile / 16 h / 85 °C 3: Dess-Martin periodane / water; dimethyl sulfoxide; 1,2-dichloro-ethane / 40 h / 0 - 80 °C 4: boron tribromide / dichloromethane / 1 h / 0 - 20 °C 5: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 5 h / Reflux; Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 0 °C 3: dimethylboron bromide / dichloromethane / 2 h / 2 - 8 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 5 h / Reflux; Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 0 - 20 °C 3: dimethylboron bromide / dichloromethane / 2 h / 2 - 8 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1.1: thionyl chloride / dichloromethane / 5 h / Reflux; Inert atmosphere 2.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C 2.2: 0 - 20 °C 3.1: dimethylboron bromide / dichloromethane / 2 h / 2 - 8 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride In dichloromethane for 5h; Reflux; Inert atmosphere; | Compound 12 can be prepared by Add 24.2g of 4-methoxyphthalic acid to the container,240 ml of dichloromethane,Slowly add 17.9ml of thionyl chloride,After the dropwise addition, the reaction was refluxed for 5 h under the protection of nitrogen;Concentrated under reduced pressure to give compound 12. | |
With thionyl chloride In dichloromethane for 5h; Reflux; Inert atmosphere; | 24.2 g of 4-methoxyphthalic acid and 240 ml of dichloromethane were added to the container, and 17.9 ml of sulfoxide was slowly added dropwise. After the dropwise addition, the reaction was refluxed for 5 h under the protection of nitrogen; and concentrated to give compound 12 under reduced pressure. | |
With thionyl chloride In dichloromethane for 5h; Reflux; Inert atmosphere; | Compound 12 can be prepared by: Add 24.2g of 4-methoxyphthalic acid and 240ml of dichloromethane to the container.17.9 ml of thionyl chloride was slowly added dropwise. After the dropwise addition, the reaction was refluxed for 5 h under the protection of nitrogen; and concentrated under reduced pressure to obtain compound 12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 5 h / Reflux; Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 0 °C | ||
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 5 h / Reflux; Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 0 - 20 °C | ||
Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 5 h / Reflux; Inert atmosphere 2.1: aluminum (III) chloride / dichloromethane / 0 - 20 °C 2.2: 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: acetic acid / 48 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: acetic acid / 48 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: acetic acid / 48 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: acetic acid / 48 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: acetic acid / 48 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: acetic acid / 48 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic anhydride / tetrahydrofuran / 4 h / Reflux 2: toluene / Molecular sieve; Reflux |
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