Chemical Properties
Yellow Oil
Uses
(R,S)-1-(2-Nitrophenyl)ethanol (cas# 3205-25-2) is a compound useful in organic synthesis.
Synthesis
General procedure for the synthesis of (S)-1-(2-nitrophenyl)ethan-1-ol from o-nitroacetophenone:
Synthesis of (RS)-1-(2-nitrophenyl)ethan-1-ol: Sodium borohydride (0.69 g, 18.16 mmol) was added in small portions to a mixed solution of 2-nitroacetophenone (1.0 g, 6.06 mmol) dissolved in methanol (9 mL) and 1,4-dioxane (6 mL) (cf. Dong et al., 2005). The reaction mixture was stirred at room temperature for 30 min and then concentrated under vacuum. The residue was diluted with ethyl acetate (50 mL) and washed sequentially with water (10 mL) and brine (10 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuum to give racemic (RS)-1-(2-nitrophenyl)ethanol (1.02 g, 100% yield).
1H NMR (400 MHz, CDCl3) data: δ 7.90 (m, 1H, Ph-H), 7.84 (m, 1H, Ph-H), 7.66 (m, 1H, Ph-H), 7.44 (m, 1H, Ph-H), 5.42 (m, 1H, Ph-CH), 2.33 (d, 1H, J = 3.5 Hz, OH), 1.58 (d, 3H, J = 5.1 Hz, CH3).
References
[1] Patent: US9200319, 2015, B2. Location in patent: Page/Page column 57
[2] Journal of Organometallic Chemistry, 2016, vol. 808, p. 68 - 77
[3] Chemistry - A European Journal, 2012, vol. 18, # 31, p. 9628 - 9637
[4] Applied Organometallic Chemistry, 2018, vol. 32, # 3,
[5] Organic Letters, 2018, vol. 20, # 11, p. 3403 - 3407
