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CAS No. : | 5043-02-7 | MDL No. : | MFCD01108716 |
Formula : | C13H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 216.23 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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% | sulfuric acid; at 80℃; for 8h; | a) 6-Methoxy-naphthalene-2-carboxylic acid methyl esterTo a solution of <strong>[2471-70-7]6-methoxy-naphthalene-2-carboxylic acid</strong> (1.01 g, 5 mmol) in methanol (10 mL), a catalytic amount of sulphuric acid was added. The mixture was then heated at 8O0C for 8 hours. Upon reaction completion (as monitored by LcMS), the solution was slowly cooled and the precipitation of the product was observed. Filtration of the white solid afforded 1.01 g (94% yield) of title compoundCi3Hi2O3Mass (calculated) [216]; (found) [M+H+] =217LC Rt = 2.43, 100% (5 min method) |
94% | sulfuric acid; at 80℃; for 8h; | Example 16 4-(4-Acetyl-[l,4]diazepan-l-yl)-N-[5-(6-methoxy-naphthalen-2-yl)-lH-pyrazol-S-yl]-butyramide a) -Methoxy-naphthalene^-carboxylic acid methyl ester; [0372] To a solution of <strong>[2471-70-7]6-methoxy-naphthalene-2-carboxylic acid</strong> (1.01 g, 5 mmol) in methanol (10 mL), a catalytic amount of sulphuric acid was added. The mixture was then heated at 80C for 8 hours. Upon reaction completion (as monitored by LCMS), the solution was slowly cooled and the precipitation of the product was observed. Filtration of the white solid afforded 1.01 g (94% yield) of title compoundC13H12O3 Mass (calculated) [216]; (found) [M+H+] =217LC Rt = 2.43, 100% (5 min method) |
94% | sulfuric acid; at 80℃; for 8h; | a) 6-Methoxy-naphthalene-2-carboxylic acid methyl ester; To a solution of <strong>[2471-70-7]6-methoxy-naphthalene-2-carboxylic acid</strong> (1.01 g, 5 mmol) in methanol (10 mL), a catalytic amount of sulphuric acid was added. The mixture was then heated at 800C for 8 hours. Upon reaction completion (as monitored by LcMS), the solution was slowly cooled and the precipitation of the product was observed. Filtration of the white solid afforded 1.01 g (94% yield) of title compound. Mass (calculated) [216]; (found) [M+H+] =217LC Rt = 2.43, 100% (5 min method) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In methanol; hexane; benzene; at 0℃; for 1h; | 6-Methoxy-2-naphthoic acid methyl ester To a stirred solution of <strong>[2471-70-7]6-methoxy-2-naphthoic acid</strong> (10.0 g, 49.5 mmol) in benzene:MeOH (4:1, 200 ML) at 0 C. was added TMS diazomethane (29.7 ML, 2.0 M in hexnae, 59.4 mmol) dropwise.After initial addition of reagent, TLC showed reaction was not quite complete, so another 4 ML of TMS diazomethane added.The reaction was then stirred for 1 h before total completion.After concentration, the residue was recrystallized from MeOH:H2O to afford the product (8.67 g, 81%) as a solid; 1H NMR (DMSO-d6) delta3.85 (s, 3H), 3.87 (s, 3H), 7.22 (dd, J=2.6, 9.0 Hz, 1H), 7.37 (d, J=2.4 Hz, 1H), 7.85-7.92 (m, 2H), 8.00 (d, J=9.0 Hz, 1H), 8.51 (s, 1H); mass spectrum [(+) ESI], m/z 217 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.2% | With dimethyl sulfate; In sodium hydroxide; | Example 3 1.5 1 of water were initially introduced into a 5 1 three-necked flask at room temperature, and 461 g of 6-hydroxy-2-naphthoic acid were then introduced. A pH of 11.5 was then established with 50% strength by weight aqueous sodium hydroxide solution and 710 g of dimethyl sulfate were subsequently allowed to run in, while cooling at 18 to 25 C., in the course of 6 hours, the pH being kept between 11.2 and 11.8 by metering in very finely divided sodium hydroxide solution via a two-component atomizing nozzle. When the reaction had ended, the solid product was filtered off with suction. 899.2 g of methyl 6-methoxy-2- naphthoate were thus obtained. This corresponds to a yield of 97.2%, based on the methylatable compounds employed. |
The methyl 6-methoxy-2-naphthoate thus obtained had a purity of more than 57% (HPLC) and contained less than 0.1% by weight of 6-hydroxy-2-naphthoic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The 2-chloromethyl-6-methoxynaphthalene used as starting material is obtained from methyl 6-methoxy-2-naphthoate by reaction with sodium dihydro-bis-(2-methoxyethoxy)aluminate to give 2-hydroxymethyl-6-methoxynaphthalene, m.p. 118-120 C. and reaction with thionyl chloride to give 2-chloromethyl-6-methoxynaphthalene, m.p. 63-65 C. by the general procedure described in Example 4 for the preparation of 2-chloromethyl-6-chloronaphthalene. |