Synthesis
M-phenoxybenzaldehyde (5 g, 25.22 mmol) was dissolved in anhydrous methanol (60 mL), cooled to 0 °C, and sodium borohydride (1.14 g, 30.26 mmol) was added in batches. The reaction mixture was stirred at room temperature for 1.5 hours and then concentrated under reduced pressure. The resulting residue was quenched with saturated aqueous ammonium chloride solution (50 mL) and extracted with ethyl acetate (3 x 50 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 3-phenoxybenzyl alcohol (5 g, 99% yield). The product was analyzed by LCMS showing [M+H]+ m/z 183.0, retention time 5.4 min, and purity 93.1% (area normalization method).
References
[1] Patent: WO2015/130905, 2015, A1. Location in patent: Paragraph 00209
[2] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6460 - 6462
[3] Journal of Organic Chemistry, 2004, vol. 69, # 5, p. 1492 - 1496
[4] Patent: WO2018/42461, 2018, A1. Location in patent: Page/Page column 7; 8
[5] Patent: US4366325, 1982, A
