2-ISO-PROPYLBENZALDEHYDE

Synthesis

GENERAL STEPS: n-Butyllithium (2.5 M hexane solution, 858 μL, 2.14 mmol) was added slowly and dropwise to an anhydrous tetrahydrofuran (THF) solution of 1-bromo-2-isopropylbenzene (388 mg, 298 μL, 1.95 mmol) at -78 °C. After maintaining the reaction temperature at -78 °C for 20 min, N,N-dimethylformamide (157 mg, 166 μL, 2.14 mmol) was added and stirring was continued at -78 °C for 20 min, followed by slow warming of the reaction mixture to -10 °C and stirring for 3 h at this temperature. Upon completion of the reaction, the reaction was quenched by the addition of water (2.5 mL) and extracted with ether (3 × 100 mL). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO), filtered and concentrated under reduced pressure to afford 2-isopropylbenzaldehyde (277 mg, quantitative yield) as a colorless oil. The structure of the product was confirmed by spectroscopic data (Ewing, 1974) and it could be used in subsequent reactions without further purification.

References

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