methyl 4-cyano-2-methylbenzoate Chemical Properties

Boiling point:

302.7±30.0 °C(Predicted)

Density 

1.15±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

Off-white to brown Solid

Safety Information

HS Code 

2926907090

methyl 4-cyano-2-methylbenzoate Usage And Synthesis

Uses

Methyl 4-cyano-2-methylbenzoate is a carboxylate derivative and can be used as an intermediate in organic synthesis.

Synthesis

Example 3.6: Preparation of methyl 4-bromo-2-methylbenzoate; Methyl 4-bromo-2-methylbenzoate (108 g, 471 mmol) was dissolved in N,N-dimethylformamide (4 L) under nitrogen protection followed by the addition of zinc(II) cyanide (88.5 g, 753.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (65 g, 56.60 mmol). The reaction mixture was stirred at 100 °C for 16 hours. After completion of the reaction, the reaction mixture was diluted with toluene for phase separation. The aqueous phase was extracted twice with toluene. All organic phases were combined and washed sequentially with brine and saturated aqueous ammonium hydroxide solution, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/cyclohexane, 1:5, v/v) to afford methyl 4-cyano-2-methylbenzoate (73 g, 89% yield).1H NMR (400 MHz, CDCl3): δ 7.78 (d, 1H), 7.52 (m, 2H), 3.92 (s, 3H), 2.62 (s, 3H).

References

[1] Patent: WO2010/127926, 2010, A1. Location in patent: Page/Page column 46
[2] Patent: WO2010/127928, 2010, A1. Location in patent: Page/Page column 32
[3] ChemBioChem, 2016, vol. 17, # 8, p. 759 - 767
[4] Patent: US2012/129832, 2012, A1. Location in patent: Page/Page column 11-12
[5] Patent: WO2013/75083, 2013, A1. Location in patent: Paragraph 00467; 00469

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