Preparation method of 1-phenylpropanol_industrial additives

Background and overview^[1]

Secondary alcohols are an important class of compounds. They are not only important organic intermediates, but are also widely used in fine chemicals such as drugs, pesticides, and spices. In the traditional method, you can use high-temperature and high-pressure hydrogenation, add inorganic reducing agents such as sodium borohydride, or use formic acid and sodium formate to prepare secondary alcohols. These methods have safety hazards in the reaction process, and produce a large amount of waste, which is harmful to the environment. Some pollution. In recent years, preparation using isopropanol as a hydrogen source, which is a cheap, safe, non-toxic hydrogen donor, has received widespread attention. However, a strong base or a weak base needs to be added during the reaction. Therefore, from the perspective of organic synthesis, a new type of organometallic catalyst is developed. By using cheap, safe, non-toxic isopropyl alcohol as the hydrogen source and solvent, there is no need to add a base during the reaction, and it can be carried out in an environmentally friendly and mild state. It is of great significance to catalyze this type of reaction. 1-Phenylpropanol is a colorless oily liquid. Molecular weight 136.19. Boiling point 219℃. Relative density 0.9915 (25/4℃). The refractive index is 1.5169 (23℃). Flash point 90℃. Miscible with methanol, ethanol, ether, benzene and toluene. Slightly aromatic. It tastes spicy and sweet. Can be used as spices and heat transfer medium. It is also a choleretic drug. It is obtained by reducing phenyl acetone with potassium borohydride in ethanol.

Preparation^[2]

1-Phenylpropanol is prepared as follows: 1-phenylacetone (134mg, 1.0mmol), cat.[Ir] (1.1mg, 0.002mmol, 0.2mol%) and isopropyl alcohol (5mL) are added to 25mL in sequence In Kirschner tube, N2 protection, reaction at 82°C for 6 hours. Cool to room temperature, remove the solvent by rotary evaporation, and then obtain the pure target compound through column chromatography (developing solvent: petroleum ether/ethyl acetate), yield: 92%. 1HNMR (500MHz, CDCl3) δ7.35-7.33 ( m, 4H), 7.29-7.26 (m, 1H), 4.60 (t, J=6.6Hz, 1H), 1.87 (brs, 1H), 1.87-1.73 (m, 2H), 0.92 (t, J=7.4Hz , 3H); 13CNMR (125MHz, CDCl3) δ144.6, 128.4, 127.5, 126.0, 31.9, 10.1.

Main reference materials

[1] Concise Dictionary of Fine Chemicals

[2] CN201710683910.8 A method of synthesizing secondary alcohols