Synthetic Route of 707-07-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 707-07-3, name is (Trimethoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
To a cooled (-78C) solution of 25 (200mg, 0.26mmol), in dry THF (2.6mL), was slowly added a solution of LiAlH4 (2M in THF, 130muL, 0.26mmol). The reaction mixture was stirred 30min at -78C, warmed to room temperature, and stirred 1h at room temperature. The reaction mixture was quenched with saturated aqueous NH4Cl and then extracted with t-BuOMe. The combined organic layer was washed with brine, dried (Na2SO4), and then concentrated under reduced pressure (water bath at room temperature). The residue was dissolved in dry CH2Cl2 (1mL) and CSA (6mg, 0.026mmol) and PhC(OMe)3 (160muL, 1.3mmol) were added. The reaction mixture was stirred overnight at room temperature, quenched with aqueous saturated NaHCO3, and then extracted with CH2Cl2. The combined organic layer was washed with brine, dried (Na2SO4), and then concentrated under reduced pressure (water bath at room temperature) and dried under strong vacuum. The residue was dissolved in dry CH2Cl2 (3mL), cooled at 0C, and then TMSCN (326muL, 2.6mmol) was added followed by the addition of BF3-Et2O (27muL, 0.26mmol). The reaction mixture was stirred 2h at 0C, warmed to room temperature and stirred 2h at room temperature. The reaction mixture was quenched with saturated aqueous NaHCO3 and then extracted with CH2Cl2. The combined organic layer was washed with brine, dried (MgSO4), and then concentrated under reduced pressure. The crude was purified on silica gel (10% t-BuOMe in heptane) to give 4 (160mg, 74%) as a clear viscous oil:
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, (Trimethoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Picard, Sebastien; Crich, David; Tetrahedron; vol. 69; 26; (2013); p. 5501 – 5510;,
Ether – Wikipedia,
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