Crotyl chloride → HCID 67550030, compound

Participants

Reaction Steps

8.6 g of 4′-hydroxy-4-biphenylcarboxylic acid was added to hydrous ethanol containing 5.3 g of potassium hydroxide dissolved therein, followed by stirring at room temperature for 30 minutes. While heating at reflux, 5.5 g of crotyl chloride was added dropwise, followed by heating at reflux for 2 hours. After the completion of the reaction, ethanol was distilled off under reduced pressure and 50 ml of 18% HCl was added to deposit a crystal. The deposited crystal was collected by filtration, washed with water and then dried under reduced pressure to obtain 5.3 g of 4′-(2-butenyloxy)-4-biphenylcarboxylic acid (XI-k). Excess thionyl chloride was added, followed by heating at reflux for 2 hours. After the completion of the reaction, excess thionyl chloride was distilled off under reduced pressure. Then, 30 ml of pyrimidine and 2.6 g of (R)-1-(3-methoxyphenyl)ethanol (XI-l) were added to the resulting crude product and the reaction was conducted at 50° C. for one hour. After the completion of the reaction, the reaction product was extracted with toluene in the presence of hydrochloric acid, washed with water and dried, and then the solvent was distilled off under reduced pressure. The residue was recrystallized from methanol to obtain 5.1 g of 1-(3-methoxyphenyl)ethyl (R)-4′-(2-butenyloxy)-4-biphenylcarboxylate (R-isomer of the compound represented by the formula (XI-m).

Provenance & Evidence