2 4 6-Trichlorobenzyl alcohol 97

Uses

2,4,6-Trichlorobenzyl Alcohol is an intermediate in the synthesis of 1,3,5-Trichloro-2-methylbenzene (T774363). 1,3,5-Trichloro-2-methylbenzene can be used as reactant/reagent in hydrodechlorination process and catalysts for the production of 2,6-dichlorotoluene from polychlorotoluene-containing mixtures. Also, it is derived from 2,4,6-Trichlorobenzoic Acid (T774715), which is a possible degradation intermediate of Polychlorinated Biphenyls (PCBs) in contaminated soil, suggesting the occurrence of microbial transformation processes over time.

Synthesis

Step 1) Commercially available 2,4,6-trichlorobenzoic acid (22.5 g, 0.1 mol) was dissolved in tetrahydrofuran (200 mL) under nitrogen protection and cooled in an ice bath. Borane-dimethyl sulfide complex (10 M, 20 mL, 0.2 mol) was added slowly. The reaction mixture was gradually warmed to 22 °C and stirred overnight under reflux conditions. Subsequently, methanol (100 mL) was added slowly and stirring was continued for 16 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure to afford 2,4,6-trichlorobenzyl alcohol (22.7 g, 100% yield) as a white solid.1H NMR (CDCl3, 400 MHz) δ: 7.37 (s, 2H), 4.93 (d, 2H, J = 6.8 Hz).

References

[1] Patent: WO2013/72300, 2013, A1. Location in patent: Page/Page column 123-124
[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 36, p. 10596 - 10599
[3] Angew. Chem., 2015, vol. 127, p. 10742 - 10745,4
[4] Patent: US6348474, 2002, B1. Location in patent: Page column 126