3-Nitrophenethyl alcohol

Uses

3-Nitrophenethyl alcohol has been employed as substrate to engineer nitrobenzene dioxygenase for the production of the highly potent antioxidant, hydroxytyrosol.

Synthesis

Under nitrogen protection, 200 mg of 3-nitrophenylacetic acid was dissolved in 2 mL of anhydrous tetrahydrofuran and 1 mL of borane-tetrahydrofuran solution (1 M) was added slowly and dropwise. The reaction mixture was stirred at room temperature for 12 h, during which the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, a small amount of water was carefully added dropwise to quench the reaction. Subsequently, the reaction system was adjusted to alkaline by adding excess saturated sodium bicarbonate solution. Extraction was carried out with ethyl acetate and the organic layer was separated, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the crude product. Finally, purification by column chromatography afforded 125 mg of 3-nitrophenylethanol (Intermediate XVI) in 68% yield.

References

[1] Patent: CN103787992, 2016, B. Location in patent: Paragraph 0309-0312
[2] Patent: WO2014/182829, 2014, A1. Location in patent: Page/Page column 55
[3] Patent: WO2016/191172, 2016, A1. Location in patent: Page/Page column 78
[4] Helvetica Chimica Acta, 1973, vol. 56, p. 2460 - 2479
[5] Journal of the American Chemical Society, 1982, vol. 104, # 7, p. 1937 - 1951