Difference between revisions of "Preparation of coumaryl alcohol"
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The experiment performed is based off of a [https://pubs.acs.org/doi/10.1021/jf506221p published paper] in which the authors previously synthesized coumaryl alcohol. The "Synthesis of p-Coumaryl Alcohol" subheading is what's important. | The experiment performed is based off of a [https://pubs.acs.org/doi/10.1021/jf506221p published paper] in which the authors previously synthesized coumaryl alcohol. The "Synthesis of p-Coumaryl Alcohol" subheading is what's important. | ||
* Initial procedure for the Synthesis of Coumaryl Alcohol (simplified): | * Initial procedure for the Synthesis of Coumaryl Alcohol (simplified): | ||
| − | # Add 1g p-Coumaric acid and 5mL acetyl chloride into a round bottom flask containing 50mL dry ethanol. | + | # Add 1g (0.0061 moles) of p-Coumaric acid and 5mL (0.07 moles) acetyl chloride into a round bottom flask containing 50mL of dry ethanol. The total concentrations of coumaric acid and acetyl chloride in solution should be 0.111M and 1.27M each. |
| − | # Stir at room temperature for 17 hours | + | # Stir at room temperature for 17 hours. |
| + | # After 17 hours, evaporate the solvent. | ||
| + | # Repeat steps 1-3 again. | ||
| + | # Recrystallize the product from ethyl acetate (product should be ethyl p-coumarate). | ||
Revision as of 05:24, 13 October 2021
Joseph Sampson, 10/21/21
This is a continuation of a project started in 2018 by A. Tibbs.
Coumaryl alcohol is a monomer of lignin.
Coumaryl alcohol will be synthesized from coumaric acid through two separate reactions:
- First, coumaric acid will be converted into ethyl coumarate by through esterification. This will involve converting the carboxylic acid group into an ethyl ester group.
- Finally, ethyl coumarate will be converted into coumaryl alcohol through a reduction reaction.
The experiment performed is based off of a published paper in which the authors previously synthesized coumaryl alcohol. The "Synthesis of p-Coumaryl Alcohol" subheading is what's important.
- Initial procedure for the Synthesis of Coumaryl Alcohol (simplified):
- Add 1g (0.0061 moles) of p-Coumaric acid and 5mL (0.07 moles) acetyl chloride into a round bottom flask containing 50mL of dry ethanol. The total concentrations of coumaric acid and acetyl chloride in solution should be 0.111M and 1.27M each.
- Stir at room temperature for 17 hours.
- After 17 hours, evaporate the solvent.
- Repeat steps 1-3 again.
- Recrystallize the product from ethyl acetate (product should be ethyl p-coumarate).