Phenol → Phenyl 3-phenylprop-2-enoate

Participants

Reaction Steps

To a 1-L three-neck flask, under a nitrogen gas stream, trans-cinnamic acid chloride (100 g, 0.60 mol), phenol (59.3 g, 0.63 mol), and THF (500 ml) were fed, and a THF solution (100 ml) of triethylamine (63.8 g, 0.63 mol) were added dropwise using a dripping funnel while being chilled with ice. After the completion of dropwise addition, 12-hour stirring was performed at room temperature, and the reaction solution was poured into water. The obtained white precipitate was filtered and dried under reduced pressure, and thereafter the yield was 135.5 g (yield rate of 99.9%). This was dissolved into approximately 200 ml of methanol by heating, and then cooled. As a result, white crystal was obtained (112.6 g, yield rate of 83.8%). Note that, the obtained crystal was confirmed to be a target trans-cinnamic acid phenyl ester by NMR structural analysis.

Provenance & Evidence