10-camphor sulfonic acid acts as a catalyst in protecting group chemistry
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Peer-reviewed literature and chemical references demonstrate that 10-camphor sulfonic acid functions as an effective catalyst for the protection of carbonyl groups in organic chemistry.
# Role of 10-camphor sulfonic acid as a catalyst in protecting group chemistry
- Tags: organic-chemistry, experimental-chemistry, equilibrium
- Score: 7
- Views: 2,981
- Answers: 1
- Asked by: Petrichorr (419 rep)
- Asked on: Oct 21, 2017
- Last active: Oct 21, 2017
- License: CC BY-SA 3.0
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## Question
I recently did a reaction in the lab where 10-camphor sulfonic acid was used as the catalyst instead of something more conventional like hydrochloric acid or sulfuric acid. Dry acetontrile was used as a solvent. The scheme is shown below:
[](https://i.sstatic.net/8skiJ.png)
I'm not too sure why it is used. My initial thoughts are it's due to the solubility of 10-CSA in water/organic solvents. Alongside this using a conventional acid such as hydrochloric acid, the water content of the acid may affect the equilibrium. Although 10-CSA still has water in it, it would not be comparable to hydrochloric or sulfuric acid. 10-CSA also is quite bulky, which could provide some selectivity on which positions are deprotonated, although I don't see this as being likely due to its conjugate base having such a high pKa. Aside f
ltistep synthesis against various reagents for a counter-reaction. The effort towards developing an efficient methodology for the protection of car-bonyl functional group is always a demanding reaction. The protection of carbonyl compounds for in-hibiting their chemical reactivity is an important operation in chemistry. In this paper, camphor sulfonic acid-catalysed protection of various carbonyl compounds is developed. This method is simple, envi-ronmentally friendly and yields products in high yields. Method:
Commercially available camphor sulfonic acid is used as organo-catalyst for the protection of carbonyl functionality. This catalyst is also employed for the protection of carbonyl functionality as thi-oacetal/mixed ketal in excellent yield. The newly synthesize compounds are characterized using 1HNMR, 13C NMR and IR spectroscopy. Result:
A diverse carbonyl functional group is protected in excellent yield under mild reaction condi-tions. Conclusion:
We have developed an efficient organocatalysed protection method of carbonyl function-ality applicable to wide range of substrates Keywords: 1,3-dioxolane; acetal; camphor sulfonic acid; ketal; organocatalysis; protection; thioketalization 1. Introduction
The chemistry of carbonyl group is very fascinating because it reacts with a wide range of reagents with or without any activation. To develop an effective synthesis, protection of carbonyl group is required in some examples. Therefore, methods are developed for the protection of carbonyl compounds and various protective groups can be used [ 1 ]. Acetal, 1-3-dioxalane, mixed ketal and thioketal are the widely used protective groups. Aldehydes and ketones are the most common groups that are protected by these methods. Importantly, these protective groups can also be removed to regenerate the original starting compounds. In many examples, the protected compounds are used as the key intermediates for the synthesis of natural products [ 2 ].
Protection of carbonyl com
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