2-Methyl-[1,1'-biphenyl]-3-carbaldehyde

Synthesis

General procedure for the synthesis of 2-methyl-[1,1'-biphenyl]-3-carbaldehyde from 2-methyl-3-phenylbenzenemethanol: To a solution of dichloromethane (60 mL) containing (2-methylbiphenyl-3-yl)methanol (TCI, Art. No. H0777, 4.12 g, 20.8 mmol) was slowly added Dess-Martin periodinane ( 9.25 g, 21.8 mmol). The reaction mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was washed sequentially with saturated NaHCO3 solution, water and brine. The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by fast chromatography on silica gel column with gradient elution of hexane solution with eluent from 0 to 30% ethyl acetate to obtain the target product 2-methyl-[1,1'-biphenyl]-3-carboxaldehyde (3.30 g, 80% yield).Results of LC-MS analysis: Calculated value of C14H13O(M + H)+: m/z = 197.2; Measured value: 197.2.

References

[1] Patent: US2017/320875, 2017, A1. Location in patent: Paragraph 0298-0299
[2] Patent: US2018/177784, 2018, A1. Location in patent: Paragraph 0522-0523
[3] Patent: WO2017/87777, 2017, A1. Location in patent: Page/Page column 61-62