A Three Step Synthesis of Trans-Cinnamaldehyde

A three step synthesis of trans-cinnamaldehyde

A three step synthesis was performed to synthesize trans-cinnamaldehyde from cinnamic acid. Trans-cinnamaldehyde is the major component that contributes to cinnamon’s distinct taste and smell. It was first isolated form the bark of cinnamon trees and tends to be very potent. It may also be found in some agricultural fungicides. The first step was synthesizing cinnamyl chloride from cinnamic acid using distilled thionyl chloride in an addition-elimination reaction. The resulting chloride was reduced to cinnamyl alcohol using sodium borohydride in hydrochloric acid and tetrahydrofuran as a solvent. A green strategy was implemented at this step by using cyclopentyl methyl ether in place of tetrahydrofuran. This was done because cyclopentyl methyl ether allows greater variability in reaction conditions, has a higher boiling pint, has limited solubility in water, and has a lower volatility which contributes to a more environmentally friendly reaction. Finally the cinnamyl alcohol was oxidized. This created the final product, trans-cinnamaldehyde.