In the future, you are employed as an organic chemist in a petrochemical company. You decide to quickly prepare the ester ethyl-3-cyclohexylpropanoate from 3-phenyl-1-propane and ethene. Describe the process you would use.
To prepare the ester ethyl-3-cyclohexylpropanoate from 3-phenyl-1-propane and ethene, you can follow the basic steps involved in an esterification reaction:
1. Identify the reactants: In this case, the reactants are 3-phenyl-1-propane (also known as cyclohexylbenzene) and ethene (also known as ethylene).
2. Convert 3-phenyl-1-propane to its corresponding carboxylic acid: To do this, you need to oxidize the aromatic ring of the benzene to convert it into a carboxylic acid group (COOH). This can be achieved using an appropriate oxidizing agent, such as potassium permanganate (KMnO4), under acidic conditions.
3. Prepare the acyl chloride: Since you want to prepare an ester, you need to convert the carboxylic acid into its acyl chloride form. This can be done by reacting the carboxylic acid with thionyl chloride (SOCl2) or oxalyl chloride (COCl)2 in the presence of a base, such as pyridine (C5H5N). This step is important as it facilitates the esterification process.
4. React the acyl chloride with ethene: In this step, you add the acyl chloride prepared in the previous step to a reaction vessel containing ethene. Since the acyl chloride is more reactive than the carboxylic acid, it readily reacts with ethene to form the desired ester.
5. Convert the ester to the desired ethyl ester: The final step involves adding ethanol (C2H5OH) to the reaction mixture obtained in the previous step. This helps in converting the intermediate ester to the desired ethyl ester.
It's important to note that the reaction conditions, such as temperature, pressure, and catalyst selection, may need to be optimized for better yield and selectivity. Additionally, purification techniques such as distillation or recrystallization may be required to isolate the desired product.
Remember to always follow proper safety guidelines and regulations when working with chemicals.