Chemical Properties
white to light yellow crystal powde
Uses
2,4,6-Trimethylbenzyl Chloride (cas# 1585-16-6) is a compound useful in organic synthesis.
General Description
α
2-Chloroisodurene undergoes coupling reaction with methylmagnesium iodide to yield 1,2-dimesitylethane.
Synthesis
General procedure for the synthesis of 2,4,6-trimethylbenzyl chloride from 2,4,6-trimethylbenzyl alcohol: 2,4,6-trimethylbenzyl alcohol (150 mg, 1.0 mmol) was dissolved in dichloromethane (DCM, 4 mL). Thionyl chloride (87 μL, 1.2 mmol) was added slowly at 0 °C. The reaction mixture was stirred for 1 h at room temperature. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to afford the target product 2,4,6-trimethylbenzyl chloride (168 mg, 100% yield) as a white powder. The product was identified by 1H NMR (300 MHz, CDCl3): δ 2.29 (s, 3H), 2.42 (s, 6H), 4.68 (s, 2H), 6.89 (s, 2H). Mass spectrometry analysis showed [M + H]+ peak at 133.
References
[1] Patent: WO2016/16238, 2016, A1. Location in patent: Page/Page column 126
[2] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1397 - 1405
[3] Organic Letters, 2002, vol. 4, # 11, p. 1975 - 1977
[4] Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 382 - 389
[5] Synlett, 2014, vol. 25, # 18, p. 2639 - 2643
