Potassium Iodide → (E)-Hex-3-ene-2,5-diol 5-acetoxy isophthaloyl chloride

Participants

Reaction Steps

A solution of 2(E)-hex-3-ene-2,5-diol (122) (0.441 g, 3.8 mmol), 5-acetoxy isophthaloyl chloride (117) (1.044 g, 4.0 mmol), a catalytic amount of 1,4-diazabicyclo[2.2.2]octane, and a catalytic amount of potassium iodide in 20 mL of pyridine was brought to 50° C. while stirring under nitrogen. After 24 hours, butanediol (0.072 g, 0.8 mmol) diluted in 10 mL of pyridine was added to the reaction mixture using a syringe pump over 8 hours. The solution was then quenched in 200 mL of cold 1N hydrochloric acid. The polymer precipitate was collected by filtration, redissolved in tetrahydrofuran, and precipitated in 100 mL of cold 1N hydrochloric acid. The polymer is then collected by filtration and dried under high vacuum. The polymer was found to have a molecular weight of ˜12,000 g/mol by GPC.

Provenance & Evidence