Preparation of coumaryl alcohol

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:

1. 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.
2. 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):

1. Add 1g p-Coumaric acid and 5mL acetyl chloride into a round bottom flask containing 50mL dry ethanol.
2. Stir at room temperature for 17 hours