No renderable structure data available
COCOC1=CC=CC=C1C=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-(methoxymethoxy)benzaldehyde |
|---|---|
| IUPAC Name | — |
| CAS Number | 5533-04-0 |
| Database ID | 10877485 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-(methoxymethoxy)benzaldehyde (CAS 5533-04-0) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 10877485
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b1474b24aa8e41a5ac7b5e01c542905dConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-ad1aec33c6fb4e72bde8da814adc4722Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 1.6M solution of n-butyl lithium in hexane (140 ml) was placed in a 1 1 flask and cooled in an ice bath. To this was added with stirring 34 ml of tetramethylethylenediamine and, after a 10 min reaction period, 34.5 g of 1-chloro-2-methoxymethoxybenzene (dropwise over a 30 min period). A pale orange suspension formed and this was stirred for 4 hours continuing the ice bath cooling. A solution of 34.5 g of 2-methoxymethoxybenzaldehyde in 30 ml of tetrahydrofuran was added with stirring and cooling. The reaction was exothermic. When the addition was complete, the mixture was allowed to warm to room temperature and was then quenched carefully with water. The resulting mixture was poured into a mixture of 1 l of ethyl acetate and 500 ml of aqueous ammonium chloride. The phases were separated and the organic phase was extracted twice with water and once with brine, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a viscous, pale orange oil. This was purified by filtration chromatography, eluting with mixtures of hexane and dichloromethane starting with pure hexane and ending with pure dichloromethane, to obtain 52.2 g (77 percent of theory) of the title compound as a pale yellow oil. The proton and carbon NMR and infrared spectra were consistent with the assigned structure. cooled in an ice bath To this was added A pale orange suspension formed cooling with stirring cooling When the addition was then quenched carefully with water The resulting mixture was poured into a mixture of 1 l of ethyl acetate and 500 ml of aqueous ammonium chloride The phases were separated the organic phase was extracted twice with water and once with brine dried over magnesium sulfate filtered concentrated by evaporation under reduced pressure to obtain a viscous, pale orange oil This was purified by filtration chromatography eluting with mixtures of hexane and dichloromethane starting with pure hexane
Source ID: ord-6a8efadcecc7440aa3952d73425bdf71Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A Grignard reagent was prepared from 1-bromo-4-ethyl-thiobenzene (1.1 g), magnesium (0.12 g), a catalytic amount of iodine and tetrahydrofuran (5 mL) in the usual manner. To the obtained Grignard reagent solution was added a solution of 2-(methoxymethoxy)benzaldehyde (0.56 g) in tetrahydrofuran (12 mL), and the mixture was stirred at 65° C. for 10 minutes. After cooling to ambient temperature, a saturated aqueous ammonium chloride solution (5 mL) and water (20 mL) were added to the reaction mixture, and the mixture was extracted with ethyl acetate (80 mL). The extract was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, then the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1) to give a diphenylmethanol compound (0.91 g). The obtained diphenylmethanol compound (0.90 g) was dissolved in dichloromethane (15 mL). To the solution was added a Dess-Martin reagent (1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one) (1.5 g), and the mixture was stirred at 25° C. for 26 hours. To the reaction mixture were added diethyl ether (75 mL) and 1 mol/L aqueous sodium hydroxide solution (30 mL), the mixture was stirred vigorously, and the organic layer was separated. The organic layer was washed with 1 mol/L aqueous sodium hydroxide solution (30 mL), water (30 mL, 3 times) and brine (30 mL), dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=15/1-9/1) to afford a ketone compound (0.82 g). A mixture of the obtained ketone compound (0.81 g), p-toluene-sulfonic acid monohydrate (0.10 g) and methanol (14 mL) was stirred at 60° C. for 4 hours. After cooling to ambient temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=15/1) to give a deprotected compound (0.69 g). The obtained deprotected compound (0.68 g) was dissolved in tetrahydrofuran (11 mL), triethylamine (0.41 mL) and methyl chloroformate (0.22 mL) were added to the solution, and the mixture was stirred at 25° C. for 1 hour. Furthermore, triethylamine (0.1 mL) and methyl chloroformate (0.061 mL) were added to the reaction mixture, and the mixture was stirred for 30 minutes. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (14 mL) and water (7 mL), sodium borohydride (0.40 g) was added to the solution, and the mixture was stirred at 25° C. for 7 hours. To the reaction mixture was added dropwise 1 mol/L hydrochloric acid (15 mL), and the mixture was extracted with ethyl acetate (75 mL). The extract was washed with water (20 mL), a saturated aqueous sodium hydrogen carbonate solution (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=8/1) to give 2-(4-ethyl-thiobenzyl)phenol (0.62 g). After cooling to ambient temperature the mixture was extracted with ethyl acetate (80 mL) The extract was washed with water (20 mL) and brine (20 mL) dried over anhydrous sodium sulfate the solvent was removed under reduced pressure The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1)
Source ID: ord-1744d852a9ff4ba6ac17056c7a033a2cConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Methoxymethoxybenzaldehyde (16.4 g) was suspended in nitromethane (54 mL), added with ammonium acetate (5.95 g), and stirred for 30 minutes at 80° C. After cooling to room temperature, the solvent was evaporated under reduced pressure and the residue was suspended in water and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated brine in order and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure. The residues were purified by diol silica gel column chromatography (5% ethyl acetate/hexane) to obtain the title compound (11.6 g) as a yellow oil. After cooling to room temperature the solvent was evaporated under reduced pressure extracted with ethyl acetate The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated brine in order dried over anhydrous sodium sulfate The solvent was then evaporated under reduced pressure The residues were purified by diol silica gel column chromatography (5% ethyl acetate/hexane)
Source ID: ord-7b8eb08023334a7e8fd968674c7f46bfConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Methoxymethoxybenzaldehyde (16.4 g) was suspended in nitromethane (54 mL), added with ammonium acetate (5.95 g), and stirred for 30 minutes at 80° C. After cooling to room temperature, the solvent was evaporated under reduced pressure and the residue was suspended in water and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated brine in order and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure. The residues were purified by diol silica gel column chromatography (5% ethyl acetate/hexane) to obtain the title compound (11.6 g) as a yellow oil. After cooling to room temperature the solvent was evaporated under reduced pressure extracted with ethyl acetate The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated brine in order dried over anhydrous sodium sulfate The solvent was then evaporated under reduced pressure The residues were purified by diol silica gel column chromatography (5% ethyl acetate/hexane)
Source ID: ord-7b8eb08023334a7e8fd968674c7f46bfConditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A tetrahydrofuran solution (30 mL) of the intermediate compound was prepared by the same method described in Example 6 except that 2-methoxymethoxybenzaldehyde (1.2 g) synthesized in the above-described Synthesis Example 2 was used instead of 2,6-dimethylbenzaldehyde (0.65 g). A 6 N hydrochloric acid solution (1 mL) was added to the tetrahydrofuran solution, and the mixture was stirred at 25° C. for 12 hours. After confirmation of the degree of reaction progress by TLC, the reaction was quenched with an aqueous solution of sodium hydrogen carbonate, and the organic phase was extracted with ethyl acetate. The resulting organic phase was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to obtain 1.9 g (yield: 84%) of [4-(2,2-diphenylvinyl)phenyl]-(2-hydroxyphenyl)methanone (10) as yellow crystals. The structure of Product 10 was confirmed by 1H-NMR. Table 1 shows optical characteristics and practical utility of Product 10. synthesized in the above-described Synthesis Example 2 After confirmation of the degree of reaction progress by TLC the reaction was quenched with an aqueous solution of sodium hydrogen carbonate the organic phase was extracted with ethyl acetate The resulting organic phase was dried over anhydrous magnesium sulfate concentrated recrystallized
Source ID: ord-b23a58b35a534179bdcc55c2b6d057daConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Salicylaldehyde (3 g) was slowly added to a N,N-dimethylformamide solution (50 mL) of sodium hydride (55%, 1.2 g) at 0° C. The mixture was stirred at the same temperature for 1 hour. Subsequently, chloromethylmethyl ether (2.9 g) was added thereto. After confirmation of the degree of reaction progress by TLC, the reaction was quenched with an aqueous solution of ammonium chloride. The organic layer was extracted with ethyl acetate and then was dried over anhydrous magnesium sulfate. The crude product obtained by concentrating the organic phase was purified by column chromatography to obtain 3.9 g (yield: 96%) of 2-methoxymethoxybenzaldehyde. After confirmation of the degree of reaction progress by TLC the reaction was quenched with an aqueous solution of ammonium chloride The organic layer was extracted with ethyl acetate was dried over anhydrous magnesium sulfate The crude product obtained by concentrating the organic phase was purified by column chromatography
Source ID: ord-1429deee810644a894868ee1518d1230Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Salicylaldehyde (3 g) was slowly added to a N,N-dimethylformamide solution (50 mL) of sodium hydride (55%, 1.2 g) at 0° C. The mixture was stirred at the same temperature for 1 hour. Subsequently, chloromethylmethyl ether (2.9 g) was added thereto. After confirmation of the degree of reaction progress by TLC, the reaction was quenched with an aqueous solution of ammonium chloride. The organic layer was extracted with ethyl acetate and then was dried over anhydrous magnesium sulfate. The crude product obtained by concentrating the organic phase was purified by column chromatography to obtain 3.9 g (yield: 96%) of 2-methoxymethoxybenzaldehyde. After confirmation of the degree of reaction progress by TLC the reaction was quenched with an aqueous solution of ammonium chloride The organic layer was extracted with ethyl acetate was dried over anhydrous magnesium sulfate The crude product obtained by concentrating the organic phase was purified by column chromatography
Source ID: ord-1429deee810644a894868ee1518d1230Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 1.6M solution of n-butyl lithium in hexane (140 ml) was placed in a 1 l flask and cooled in an ice bath. To this was added with stirring 34 ml of tetramethylethylenediamine and, after a 10 min reaction period, 34.5 g of 1-chloro-2-methoxymethoxybenzene (dropwise over a 30 min period). A pale orange suspension formed and this was stirred for 4 hours continuing the ice bath cooling. A solution of 34.5 g of 2-methoxymethoxybenzaldehyde in 30 ml of tetrahydrofuran was added with stirring and cooling. The reaction was exothermic. When the addition was complete, the mixture was allowed to warm to room temperature and was then quenched carefully with water. The resulting mixture was poured into a mixture of 1 l of ethyl acetate and 500 ml of aqueous ammonium chloride. The phases were separated and the organic phase was extracted twice with water and once with brine, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a viscous, pale orange oil. This was purified by filtration chromatography, eluting with mixtures of hexane and dichloromethane starting with pure hexane and ending with pure dichloromethane, to obtain 52.2 g (77 percent of theory) of the title compound as a pale yellow oil. The proton and carbon NMR and infrared spectra were consistent with the assigned structure. cooled in an ice bath To this was added A pale orange suspension formed cooling with stirring cooling When the addition was then quenched carefully with water The resulting mixture was poured into a mixture of 1 l of ethyl acetate and 500 ml of aqueous ammonium chloride The phases were separated the organic phase was extracted twice with water and once with brine dried over magnesium sulfate filtered concentrated by evaporation under reduced pressure to obtain a viscous, pale orange oil This was purified by filtration chromatography eluting with mixtures of hexane and dichloromethane starting with pure hexane
Source ID: ord-a21853dddf7944e7ad1fc4c089ffb133Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 1.6M solution of n-butyl lithium in hexane (140 ml) was placed in a 1 1 flask and cooled in an ice bath. To this was added with stirring 34 ml of tetramethylethylenediamine and, after a 10 min reaction period, 34.5 g of 1-chloro-2-methoxymethoxybenzene (dropwise over a 30 min period). A pale orange suspension formed and this was stirred for 4 hours continuing the ice bath cooling. A solution of 34.5 g of 2-methoxymethoxybenzaldehyde in 30 ml of tetrahydrofuran was added with stirring and cooling. The reaction was exothermic. When the addition was complete, the mixture was allowed to warm to room temperature and was then quenched carefully with water. The resulting mixture was poured into a mixture of 1 l of ethyl acetate and 500 ml of aqueous ammonium chloride. The phases were separated and the organic phase was extracted twice with water and once with brine, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a viscous, pale orange oil. This was purified by filtration chromatography, eluting with mixtures of hexane and dichloromethane starting with pure hexane and ending with pure dichloromethane, to obtain 52.2 g (77 percent of theory) of the title compound as a pale yellow oil. The proton and carbon NMR and infrared spectra were consistent with the assigned structure. cooled in an ice bath To this was added A pale orange suspension formed cooling with stirring cooling When the addition was then quenched carefully with water The resulting mixture was poured into a mixture of 1 l of ethyl acetate and 500 ml of aqueous ammonium chloride The phases were separated the organic phase was extracted twice with water and once with brine dried over magnesium sulfate filtered concentrated by evaporation under reduced pressure to obtain a viscous, pale orange oil This was purified by filtration chromatography eluting with mixtures of hexane and dichloromethane starting with pure hexane
Source ID: ord-6a8efadcecc7440aa3952d73425bdf71Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b1474b24aa8e41a5ac7b5e01c542905dPubChem References
These sources are listed in the compound's public database record.
Request a Quote
Send the required specification, quantity, destination and intended use. The CATO team will review availability and respond.