Structure of 3,5-Di-tert-butylbenzaldehyde
CAS No.: 17610-00-3
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CAS No. : | 17610-00-3 |
Formula : | C15H22O |
M.W : | 218.33 |
SMILES Code : | O=CC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1 |
MDL No. : | MFCD00026298 |
InChI Key : | BRUITYMDHWNCIG-UHFFFAOYSA-N |
Pubchem ID : | 1268253 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
* 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 |
---|---|---|
47% | With sodium hydrogencarbonate; In ethanol; at 100 - 120℃; for 0.333333h;Microwave irradiation; | General procedure: A mixture of the corresponding hydroxy benzaldehyde (1 equiv), N-tert-buthyl hydroxylamine hydrochloride (1.1 equiv), and sodium bicarbonate (1.1 equiv) in absolute ethanol (5 mL/mmol) as solvent was heated under microwave irradiation until the carbonyl compound was not present or there was no progress in the reaction (checked by TLC). The solvent was removed in vacuo and the reaction mixture diluted with H2O and extracted with EtOAc. After the workup of the combined organic layers, the residue was purified by column chromatography (SiO2, mixtures of petroleum ether/EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | To a solution of diisopropylamine (1.01 g, 1.4 mL, 10 mmol) in 10 ml of THF at -78 C. under nitrogen was added n-butyllithium (2.5 M in hexanes, 4 mL, 10 mmol) dropwise. After 30 minutes, to this solution was added HMPA (1.79 g, 1.74 mL, 10 mmol). The resulting solution was treated with <strong>[57876-69-4]2-chloro-3-methylquinoline</strong> (1.78 g, 10 mmol) in THF (10 mL) to afford a red solution, which was stirred for 30 minutes. To this mixture was added 3,5-bis(tert-butyl)benzaldehyde (1.09 g, 5 mmol) in THF (10 mL) at -78 C. After one hour at -78 C., the reaction mixture was quenched with saturated aqueous NH4Cl solution and treated with 30 ml of diethyl ether, and the product was extracted with three 20-ml portions of diethyl ether. The combined extracts were washed with water, dried over anhydrous MgSO4, and concentrated under vacuum. Flash chromatography (eluent: dichloromethane) afforded the alcohol L4-1 (1.40 g, 71% yield) as a yellow foam. 1H NMR (600 MHz, CDCl3) delta 8.02-8.00 (m, 1H), 7.96 (s, 1H), 7.73 (dd, J1=1.3 Hz, J1=8.1 Hz, 1H), 7.71-7.68 (m, 18H), 7.55-7.52 (m, 1H), 7.39 (t, J=1.8 Hz, 1H), 7.24 (d, J=1.8 Hz, 2H), 5.16 (t, J=6.6 Hz, 1H), 3.33 (dd, J=3.7 Hz, J2=6.6 Hz, 2H), 1.32 (s, 18H); 13C NMR (150 MHz, CDCl3) delta 151.41, 151.08, 146.62, 142.73, 139.71, 130.35, 129.87, 128.09, 127.31, 127.13, 126.92, 121.91, 119.85, 73.65, 43.37, 34.88, 31.42. |
A202849 [6136-71-6]
1-(3-(tert-Butyl)phenyl)ethanone
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