No renderable structure data available
CC1=C(C=C(C=C1)C=O)IChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-iodo-4-methylbenzaldehyde |
|---|---|
| IUPAC Name | — |
| CAS Number | 58586-55-3 |
| Database ID | 12330254 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-iodo-4-methylbenzaldehyde (CAS 58586-55-3) 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 12330254
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-495aeb6923354e85904ce6b729aedee5Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-4435d1ee7c4642cc9069997ab958f634Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-503da2740ef94b2aa53cde2f7a527fdfConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a −78° C. solution of triphenyl((2,6,6-trimethylcyclohex-1-enyl)methyl)phosphonium bromide (24) (0.3787 g, 0.79 mmol) and 18-crown-6 (0.0246 g, 0.093 mmol) in CH2Cl2 (7 mL) was added potassium tert-butoxide (0.0991 g, 0.88 mmol). The mixture was sonicated at room temperature under argon for 2 min, resulting in a deep red solution. The mixture was cooled to −78° C. then a solution of 3-iodo-4-methylbenzaldehyde (0.1742 g, 0.71 mmol) in CH2Cl2 (3 mL+2 mL) was added and stirred for 5 min. The reaction mixture was allowed to warm to room temperature. Additional phosphonium salt 24 (0.3725 g, 1.6 mmol), 3-iodo-4-methylbenzaldehyde (0.2538 g, 1.7 mmol) and potassium tert-butoxide (0.1548 g, 1.38 mmol) were then added and the reaction was stirred at room temperature for 4.3 h. The reaction was partitioned between EtOAc and water then the combined organics were washed with brine, dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (6 to 50% EtOAc-hexanes gradient) gave (E)-2-iodo-1-methyl-4-(2-(2,6,6-trimethylcyclohex-1-enyl)vinyl)benzene as a white solid. Yield (0.26 g, 45%): 1H NMR (400 MHz, DMSO-d6) δ 7.91 (d, J=1.6 Hz, 1H), 7.44 (dd, J=7.6, 1.2 Hz, 1H), 7.29 (d, J=7.2 Hz, 1H), 6.71 (d, J=16.4 Hz, 1H), 6.28 (6, J=16.8 Hz, 1H), 2.35 (s, 3H), 2.01 (t, J=6.4 Hz, 2H), 1.72 (s, 3H), 1.57-1.64 (m, 2H), 1.43-1.47 (m, 2H), 1.04 (s, 6H). The mixture was sonicated at room temperature under argon for 2 min resulting in a deep red solution to warm to room temperature the reaction was stirred at room temperature for 4.3 h The reaction was partitioned between EtOAc and water the combined organics were washed with brine dried over MgSO4 concentrated under reduced pressure Purification by flash chromatography (6 to 50% EtOAc-hexanes gradient)
Source ID: ord-5f33ccf406034e1dbb379159b510b051Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a −78° C. solution of triphenyl((2,6,6-trimethylcyclohex-1-enyl)methyl)phosphonium bromide (24) (0.3787 g, 0.79 mmol) and 18-crown-6 (0.0246 g, 0.093 mmol) in CH2Cl2 (7 mL) was added potassium tert-butoxide (0.0991 g, 0.88 mmol). The mixture was sonicated at room temperature under argon for 2 min, resulting in a deep red solution. The mixture was cooled to −78° C. then a solution of 3-iodo-4-methylbenzaldehyde (0.1742 g, 0.71 mmol) in CH2Cl2 (3 mL+2 mL) was added and stirred for 5 min. The reaction mixture was allowed to warm to room temperature. Additional phosphonium salt 24 (0.3725 g, 1.6 mmol), 3-iodo-4-methylbenzaldehyde (0.2538 g, 1.7 mmol) and potassium tert-butoxide (0.1548 g, 1.38 mmol) were then added and the reaction was stirred at room temperature for 4.3 h. The reaction was partitioned between EtOAc and water then the combined organics were washed with brine, dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (6 to 50% EtOAc-hexanes gradient) gave (E)-2-iodo-1-methyl-4-(2-(2,6,6-trimethylcyclohex-1-enyl)vinyl)benzene as a white solid. Yield (0.26 g, 45%): 1H NMR (400 MHz, DMSO-d6) δ 7.91 (d, J=1.6 Hz, 1H), 7.44 (dd, J=7.6, 1.2 Hz, 1H), 7.29 (d, J=7.2 Hz, 1H), 6.71 (d, J=16.4 Hz, 1H), 6.28 (6, J=16.8 Hz, 1H), 2.35 (s, 3H), 2.01 (t, J=6.4 Hz, 2H), 1.72 (s, 3H), 1.57-1.64 (m, 2H), 1.43-1.47 (m, 2H), 1.04 (s, 6H). The mixture was sonicated at room temperature under argon for 2 min resulting in a deep red solution to warm to room temperature the reaction was stirred at room temperature for 4.3 h The reaction was partitioned between EtOAc and water the combined organics were washed with brine dried over MgSO4 concentrated under reduced pressure Purification by flash chromatography (6 to 50% EtOAc-hexanes gradient)
Source ID: ord-5f33ccf406034e1dbb379159b510b051Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The product from Example 1C (0.34 g, 3.0 mmol), the product from Example 3A (0.74 g, 3.0 mmol) and methyl 3-aminocrotonate (0.35 g, 3.0 mmol) in methanol (8 mL) were heated to 80° C. in a sealed tube for 60 hours. After cooling to ambient temperature, the mixture was filtered and the filter cake washed with methanol and dried to provide the title compound (0.60 g). the mixture was filtered the filter cake washed with methanol dried
Source ID: ord-42be9a9624214975863e00402913c28eConditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Iodo-4-methylbenzoic acid (1.0 g, 3.96 mmol) in dry CH2Cl2:THF 1:1 (200 mL) was treated with oxalyl chloride (1 mL, 11.9 mmol) and several drops of N,N-dimethylformamide. The mixture was heated at 65° C. for 30 minutes, allowed to cool to ambient temperature, and concentrated under reduced pressure to provide a light yellow solid. The obtained solid was dissolved in THF (200 mL) and treated with a 1M solution of lithium tri-tert-butoxyaluminohydride in THF (4.1 mL, 4.1 mmol) via syringe at −78° C. After 30 minutes at −78° C., a saturated solution of Rochelle's salt was added and the mixture was allowed to warm to ambient temperature. The organic layer was washed in succession with 1N HCl, saturated NaHCO3 and brine, dried over Na2SO4, and concentrated. The resulting residue was purified by flash chromatography using hexanes:ethyl acetate (4:1) as the eluent to provide the title compound as a white solid (300 mg, 18%). to cool to ambient temperature concentrated under reduced pressure to provide a light yellow solid to warm to ambient temperature The organic layer was washed in succession with 1N HCl, saturated NaHCO3 and brine dried over Na2SO4 concentrated The resulting residue was purified by flash chromatography
Source ID: ord-36a4b8a9d86842e7b09409f38ff75be7Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Iodo-4-methylbenzoic acid (1.0 g, 3.96 mmol) in dry CH2Cl2:THF 1:1 (200 mL) was treated with oxalyl chloride (1 mL, 11.9 mmol) and several drops of N,N-dimethylformamide. The mixture was heated at 65° C. for 30 minutes, allowed to cool to ambient temperature, and concentrated under reduced pressure to provide a light yellow solid. The obtained solid was dissolved in THF (200 mL) and treated with a 1M solution of lithium tri-tert-butoxyaluminohydride in THF (4.1 mL, 4.1 mmol) via syringe at −78° C. After 30 minutes at −78° C., a saturated solution of Rochelle's salt was added and the mixture was allowed to warm to ambient temperature. The organic layer was washed in succession with 1N HCl, saturated NaHCO3 and brine, dried over Na2SO4, and concentrated. The resulting residue was purified by flash chromatography using hexanes:ethyl acetate (4:1) as the eluent to provide the title compound as a white solid (300 mg, 18%). to cool to ambient temperature concentrated under reduced pressure to provide a light yellow solid to warm to ambient temperature The organic layer was washed in succession with 1N HCl, saturated NaHCO3 and brine dried over Na2SO4 concentrated The resulting residue was purified by flash chromatography
Source ID: ord-36a4b8a9d86842e7b09409f38ff75be7Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a −78° C. solution of triphenyl((2,6,6-trimethylcyclohex-1-enyl)methyl)phosphonium bromide (24) (0.3787 g, 0.79 mmol) and 18-crown-6 (0.0246 g, 0.093 mmol) in CH2Cl2 (7 mL) was added potassium tert-butoxide (0.0991 g, 0.88 mmol). The mixture was sonicated at room temperature under argon for 2 min, resulting in a deep red solution. The mixture was cooled to −78° C. then a solution of 3-iodo-4-methylbenzaldehyde (0.1742 g, 0.71 mmol) in CH2Cl2 (3 mL+2 mL) was added and stirred for 5 min. The reaction mixture was allowed to warm to room temperature. Additional phosphonium salt 24 (0.3725 g, 1.6 mmol), 3-iodo-4-methylbenzaldehyde (0.2538 g, 1.7 mmol) and potassium tert-butoxide (0.1548 g, 1.38 mmol) were then added and the reaction was stirred at room temperature for 4.3 h. The reaction was partitioned between EtOAc and water then the combined organics were washed with brine, dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (6 to 50% EtOAc-hexanes gradient) gave (E)-2-iodo-1-methyl-4-(2-(2,6,6-trimethylcyclohex-1-enyl)vinyl)benzene as a white solid. Yield (0.26 g, 45%): NMR (400 MHz, DMSO-d6) δ 7.91 (d, J=1.6 Hz, 1H), 7.44 (dd, J=7.6, 1.2 Hz, 1H), 7.29 (d, J=7.2 Hz, 1H), 6.71 (d, J=16.4 Hz, 1H), 6.28 (6, J=16.8 Hz, 1H), 2.35 (s, 3H), 2.01 (t, J=6.4 Hz, 2H), 1.72 (s, 3H), 1.57-1.64 (m, 2H), 1.43-1.47 (m, 2H), 1.04 (s, 6H). The mixture was sonicated at room temperature under argon for 2 min resulting in a deep red solution to warm to room temperature the reaction was stirred at room temperature for 4.3 h The reaction was partitioned between EtOAc and water the combined organics were washed with brine dried over MgSO4 concentrated under reduced pressure Purification by flash chromatography (6 to 50% EtOAc-hexanes gradient)
Source ID: ord-1f81ea17ae2a46e39306a46045232d6dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The product from Example 11B (0.34 g, 3.0 mmol), the product from Example 54A (0.74 g, 3.0 mmol) and methyl 3-aminocrotonate (0.35 g, 3.0 mmol) in methanol (8 mL) were processed as described in Example 68A to provide the title compound (0.60 g).
Source ID: ord-a2bc46c6315442c19bb82f7cc6e4f1eaConditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Iodo-4-methylbenzoic acid (1.0 g, 3.96 mmol) in dry CH2Cl2:THF 1:1 (200 mL) was treated with oxalyl chloride (1 mL, 11.9 mmol) and several drops of DMF. The mixture was heated at 65° C. for 30 minutes, cooled to ambient temperature, and concentrated under reduced pressure to provide a light yellow solid. The obtained solid was dissolved in THF (200 mL) and treated with a 1M solution of lithium tri-tert-butoxyaluminohydride in THF (4.1 mL, 4.1 mmol) via syringe at −78° C. After 30 minutes at −78° C., a saturated solution of Rochelle's salt was added and the mixture was allowed to warm to ambient temperature. The organic layer was washed in succession with 1N HCl, saturated NaHCO3 and brine, dried over Na2SO4, and concentrated. The resulting residue was purified by flash chromatography using hexanes:ethyl acetate (4:1) as the eluent to provide the title compound as a white solid (300 mg, 18%). cooled to ambient temperature concentrated under reduced pressure to provide a light yellow solid to warm to ambient temperature The organic layer was washed in succession with 1N HCl, saturated NaHCO3 and brine dried over Na2SO4 concentrated The resulting residue was purified by flash chromatography
Source ID: ord-fd51b15161af4b158effdcf2b4a39dfaConditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Iodo-4-methylbenzoic acid (1.0 g, 3.96 mmol) in dry CH2Cl2:THF 1:1 (200 mL) was treated with oxalyl chloride (1 mL, 11.9 mmol) and several drops of DMF. The mixture was heated at 65° C. for 30 minutes, cooled to ambient temperature, and concentrated under reduced pressure to provide a light yellow solid. The obtained solid was dissolved in THF (200 mL) and treated with a 1M solution of lithium tri-tert-butoxyaluminohydride in THF (4.1 mL, 4.1 mmol) via syringe at −78° C. After 30 minutes at −78° C., a saturated solution of Rochelle's salt was added and the mixture was allowed to warm to ambient temperature. The organic layer was washed in succession with 1N HCl, saturated NaHCO3 and brine, dried over Na2SO4, and concentrated. The resulting residue was purified by flash chromatography using hexanes:ethyl acetate (4:1) as the eluent to provide the title compound as a white solid (300 mg, 18%). cooled to ambient temperature concentrated under reduced pressure to provide a light yellow solid to warm to ambient temperature The organic layer was washed in succession with 1N HCl, saturated NaHCO3 and brine dried over Na2SO4 concentrated The resulting residue was purified by flash chromatography
Source ID: ord-fd51b15161af4b158effdcf2b4a39dfaPubChem References
These sources are listed in the compound's public database record.
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