Description
3,5-dihydroxybenzyl alcohol: a kind of critical medicine intermediate and chemical intermediate
3,5-Dihydroxybenzyl alcohol is a colourless product with a melting point of 182~186℃. It is soluble in water, ethanol, ether, THF and other polar solvents. This compound is a vital pharmaceutical and chemical intermediate and an essential raw material for organic synthesis. It can be used as a raw material to prepare pseudo-choleretic drugs with intellectual property rights in my country, such as pseudo-amyloid, bonicon, bromoprim, and resveratrol. It has antibacterial, anti-inflammatory, anti-tumour, antioxidant, anti-shock, and coronary heart disease prevention and treatment biological activities. It is mainly isolated from Veratrum ussuri and Veratrum hairy spike produced in Northeast China; it can also be used to synthesize pharmaceutical intermediates such as 3,5-dihydroxybenzaldehyde and 3,5-dihydroxybenzoyl ethyl ketone, and can also be used as an additive in the field of fine chemicals such as daily chemicals.
Chemical Properties
White to light yellow crystal powder
Uses
3,5-Dihydroxybenzyl Alcohol is a used as a dendrimer building block.
Uses
3,5-Dihydroxybenzyl alcohol may be used as monomer for the synthesis of a series of monodisperse dendritic polyether macromolecules.It may be employed in the synthesis of dimethylsilyl linked dihydroxybenzyl alcohol based dendrimers.
Application
3,5-Dihydroxybenzyl alcohol is an important multifunctional organic intermediate, with applications primarily in medicinal chemistry, polymer materials, and fine chemicals. It serves as a key building block in the synthesis of dendrimers and hyperbranched polymers, and as a starting material for the construction of complex pharmaceutical molecules with antioxidant, antitumor, or antibacterial activities. In particular, in drug discovery, it is often used as an alternative precursor for the synthesis of resveratrol analogs and other polyphenolic natural products.
General Description
Aggregation behavior of 3,5-dihydroxybenzyl alcohol based dendritic polymers has been investigated by dynamic light scattering and transmission electron microscopy. Preparation of dendritic polyether macromolecules based on 3, 5-dihydroxybenzyl alcohol building block and having carboxylate groups as chain-ends has been described.
Synthesis
Preparation of 3,5-dihydroxybenzyl alcohol: Add 50mL THF to a 250mL three-necked flask, add 3.15g (0.082mol) NaBH, 2.38g (0.01mol) 3,5-Diacetoxybenzoic acid, control the temperature at 0 degrees in an ice-water bath, slowly drop 60ml THF solution containing 9g (0.036mol) I2, and then add 4.76g (0.02mol) of the product from the previous step after the dropwise addition, heat to reflux, and track the reaction with a plate. After the reaction is completed, concentrate to dryness under reduced pressure, add 100mL saturated NaHCO solution, extract with ether, combine the organic layers, dry with anhydrous magnesium sulfate, filter, concentrate, and recrystallize with hot water to obtain 3.5g white crystals with a yield of 83.2%.
References
[1] Journal of the American Chemical Society, 2003, vol. 125, # 3, p. 650 - 651
[2] Patent: CN105622350, 2016, A. Location in patent: Paragraph 0030; 0033; 0034
[3] Journal of the American Chemical Society, 1996, vol. 118, # 18, p. 4354 - 4360
[4] Tetrahedron Letters, 2008, vol. 49, # 20, p. 3260 - 3263
[5] Patent: CN105884580, 2016, A
