No renderable structure data available
COC(=O)C1=CC=C(C=C1)C=CC=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | methyl 4-(3-oxoprop-1-enyl)benzoate |
|---|---|
| IUPAC Name | — |
| CAS Number | 78024-60-9 |
| Database ID | 53758591 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
methyl 4-(3-oxoprop-1-enyl)benzoate (CAS 78024-60-9) 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 53758591
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
11 reactions · 11 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8c31cbaa8aae4840bb48e64ce9eab98fConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-1b9976c3d9494182ac97ed2c697dd0ccConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c1e1e8948405442885ecc05afde8179cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 0.21 g (1.25 mmoles) of 4-carbomethoxybenzaldehyde, 0.42 g (1.25 mmoles) of formylmethylenetriphenylphosphorane and a catalytic amount of benzoic acid in 25 ml of THF was refluxed under nitrogen for 18 hours. The THF was evaporated and the recovered gum extracted repeatedly with ether. The combined ether extracts were evaporated. Flash chromatography on silica gel with 50% CH2Cl2 /hexane up to 100% CH2Cl2 gave 90 mg of a white solid. The THF was evaporated the recovered gum extracted repeatedly with ether The combined ether extracts were evaporated
Source ID: ord-cc38f46755a04564876d129644065ec5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 27.3 g (0.09 mole) of formyl methyltriphenyl phosphonium bromide and 14.8 g (0.09 mole) of p-carbomethoxybenzaldehyde in 900 ml of dry toluene was refluxed under nitrogen for 24 hr. After evaporating toluene under reduced pressure, the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant. The second fraction obtained by using 10% ethyl acetate in petroleum ether gave 4-carbomethoxycinnamaldehyde. Recrystallization from benzene gave 12.5 g 4-carbomethoxycinnamaldehyde, yield 73% m.p. 99°-101° C. The infrared spectrum showed absorption at 1720 cm-1 ##STR8## 1680 cm-1 (CHO), and 1620 cm-1 (--CH=CH--). NMR (CDCl3) showed δ3.8 (s, --COOCH3, 3) 6.5-7.1 (m,=CH--CHO, l), 7.3-7.6 (m, aromatic, 4), 7.9-8.1 (d, --CH=, l), and 9.8 (d, --CHO, l). Analysis calculated for C11H10O3 : C, 69.42%, H, 5.2%. Found: C, 68.69%, H, 5.25%. After evaporating toluene under reduced pressure the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant The second fraction obtained
Source ID: ord-1c632f04a7644a7f89c58413d50fda07Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 27.3 g (0.09 mole) of formyl methyltriphenyl phosphonium bromide and 14.8 g (0.09 mole) of p-carbomethoxybenzaldehyde in 900 ml of dry toluene was refluxed under nitrogen for 24 hr. After evaporating toluene under reduced pressure, the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant. The second fraction obtained by using 10% ethyl acetate in petroleum ether gave 4-carbomethoxycinnamaldehyde. Recrystallization from benzene gave 12.5 g 4-carbomethoxycinnamaldehyde, yield 73% m.p. 99°-101° C. The infrared spectrum showed absorption at 1720 cm-1 ##STR8## 1680 cm-1 (CHO), and 1620 cm-1 (--CH=CH--). NMR (CDCl3) showed δ3.8 (s, --COOCH3, 3) 6.5-7.1 (m,=CH--CHO, l), 7.3-7.6 (m, aromatic, 4), 7.9-8.1 (d, --CH=, l), and 9.8 (d, --CHO, l). Analysis calculated for C11H10O3 : C, 69.42%, H, 5.2%. Found: C, 68.69%, H, 5.25%. After evaporating toluene under reduced pressure the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant The second fraction obtained
Source ID: ord-1c632f04a7644a7f89c58413d50fda07Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8c31cbaa8aae4840bb48e64ce9eab98fConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c1e1e8948405442885ecc05afde8179cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 27.3 g (0.09 mole) of formyl methyltriphenyl phosphonium bromide and 14.8 g (0.09 mole) of p-carbomethoxybenzaldehyde in 900 ml of dry toluene was refluxed under nitrogen for 24 hours. After evaporating toluene under reduced pressure, the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant. The second fraction obtained by using 10% ethyl acetate in petroleum ether gave 4-carbomethoxycinnamaldehyde. Recrystallization from benzene gave 12.5 g 4-carbomethoxycinnamaldehyde, yield 73% m.p. 99°-101° C. The infrared spectrum showed absorption at 1720 cm1 (COOCH3), 1680 cm-1 (CHO), and 1620 cm-1 (--CH=CH--). NMR (CDCl3) showed δ3.8 (s, --COOCH3, 3) 6.5-7.1 (m,=CH--CHO, 1), 7.3-7.6 (m, aromatic, 4), 7.9-8.1 (d, --CH=, 1), and 9.8 (d, --CHO, 1 ). Analysis calculated for C11H10O3 :C, 69.42%, H, 5.2%. Found: C, 68.69%, H, 5.26%. After evaporating toluene under reduced pressure the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant The second fraction obtained
Source ID: ord-b7b99ef037e440a3b50b1cfb8248dec4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 0.21 g (1.25 mmoles) of 4-carbomethoxybenzaldehyde, 0.42 g (1.25 mmoles) of formylmethylenetriphenylphosphorane and a catalytic amount of benzoic acid in 25 ml of THF was refluxed under nitrogen for 18 hours. The THF was evaporated and the recovered gum extracted repeatedly with ether. The combined ether extracts were evaporated. Flash chromatography on silica gel with 50% CH2Cl2 /hexane up to 100% CH2Cl2 gave 90 mg of a white solid. The THF was evaporated the recovered gum extracted repeatedly with ether The combined ether extracts were evaporated
Source ID: ord-cc38f46755a04564876d129644065ec5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 27.3 g (0.09 mole) of formyl methyltriphenyl phosphonium bromide and 14.8 g (0.09 mole) of p-carbomethoxybenzaldehyde in 900 ml of dry toluene was refluxed under nitrogen for 24 hr. After evaporating toluene under reduced pressure, the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant. The second fraction obtained by using 10% ethyl acetate in petroleum ether gave 4-carbomethoxycinnamaldehyde. Recrystallization from benzene gave 12.5 g 4-carbomethoxycinnamaldehyde, yield 73% m.p. 99°-101° C. The infrared spectrum showed absorption at 1720 cm-1 ##STR8## 1680 cm-1 (CHO), and 1620 cm-1 (--CH=CH--). NMR (CDCl3) showed δ3.8 (s, --COOCH3, 3) 6.5-7.1 (m,=CH--CHO, l), 7.3-7.6 (m, aromatic, 4), 7.9-8.1 (d, --CH=, l), and 9.8 (d, --CHO, l). Analysis calculated for C11H10O3 : C, 69.42%, H, 5.2%. Found: C, 68.69%, H, 5.25%. After evaporating toluene under reduced pressure the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant The second fraction obtained
Source ID: ord-1c632f04a7644a7f89c58413d50fda07PubChem References
These sources are listed in the compound's public database record.
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