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(3S)-4-Chloro-1,3-butanediol is an important intermediate in the production of various chemicals and pharmaceuticals.
In the chemical industry, the efficient and reliable production of this compound is of critical importance.
As such, the instruction of its synthesis has been extensively studied and refined over the years.
The synthesis of (3S)-4-chloro-1,3-butanediol typically involves several steps, including the reaction of (3R)-butan-1,2-diol with chloroacetic acid, followed by hydrolysis of the resulting intermediate to yield the desired product.
The first step of this synthesis involves the production of (3R)-butan-1,2-diol, which can be synthesized via several different methods.
One common method involves the reduction of (3R)-butane-2,3-diol using a reducing agent such as lithium aluminum hydride (LiAlH4).
Once (3R)-butan-1,2-diol has been synthesized, it can be reacted with chloroacetic acid to produce (3S)-4-chloro-1,3-butanediol.
The reaction typically takes place in the presence of a solvent, such as ethyl acetate or dichloromethane, and is typically carried out at a temperature between 50°C and 100°C.
The reaction is often complete within a few hours, after which the resulting mixture is allowed to cool and the organic layer is separated and concentrated.
The next step in the synthesis of (3S)-4-chloro-1,3-butanediol is the hydrolysis of the intermediate produced in the previous step.
This can be accomplished using a strong acid, such as hydrochloric acid, in the presence of a solvent, such as water or ethanol.
The reaction typically takes place at a temperature between 20°C and 50°C and is often complete within a few hours.
Once the hydrolysis reaction is complete, the resulting mixture is typically filtered to remove any solid impurities, and the aqueous layer is extracted with an organic solvent, such as ethyl acetate or dichloromethane.
The organic layer is then dried over anhydrous sodium sulfate and concentrated to yield the desired product.
The yield and purity of (3S)-4-chloro-1,3-butanediol can be improved by optimizing the conditions of each step in the synthesis.
For example, the use of a higher concentration of (3R)-butan-1,2-diol or a stronger reducing agent can improve the yield of the first step.
Similarly, the use of a stronger acid or a longer reaction time can improve the yield of the hydrolysis step.
In addition to its use as an intermediate in the production of various chemicals and pharmaceuticals, (3S)-4-chloro-1,3-butanediol has also been studied for its potential biological activity.
For example, it has been shown to have antibacterial and antifungal properties, and it may have potential as a treatment for bacterial infections.
Further research is needed to fully understand the biological activity of this compound and to develop new applications for it.
Overall, the synthesis of (3S)-4-chloro-1,3-butanediol is a complex process that requires careful optimization of each step.
However, with the right conditions and precautions, it is possible to produce this compound in high yields and purity, making it an important intermediate in the chemical industry and a potential candidate for biological applications.