Synthesis
8A. Synthesis of 4-hydroxymethylbenzonitrile: Boron trifluoride diethyl ether compound (0.85 mL, 6.8 mmol) was slowly added to a solution containing 4-cyanobenzoic acid (1.0 g, 6.8 mmol) and tetrahydrofuran (10 mL). Borane-tetrahydrofuran complex (1.0 M, 13.6 mL) was added dropwise to the reaction mixture at room temperature, during which no significant exothermic phenomenon was observed. The reaction mixture was stirred continuously for 2 h at room temperature and then concentrated under vacuum. The obtained residue was dissolved in ethyl acetate (50 mL), washed sequentially with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated in vacuum to afford the target product 4-hydroxymethylbenzonitrile (0.900 g, 95% yield) as a white solid.1H NMR (400 MHz, CDCl3) δ 4.65 (s, 2H), 7.38 (d 2H), 7.53 (d, 2H).
References
[1] Patent: US2007/270438, 2007, A1. Location in patent: Page/Page column 39
[2] Tetrahedron Letters, 2003, vol. 44, # 16, p. 3427 - 3428
[3] Advanced Synthesis and Catalysis, 2014, vol. 356, # 2-3, p. 308 - 312
[4] Dalton Transactions, 2016, vol. 45, # 19, p. 8265 - 8271
