Thionyl Chloride → HCID 19860606, compound

Participants

Reaction Steps

Thionyl chloride (8.5 g) was added to 4.0 g of the 4'-dodecyloxy-3'-fluorobiphenyl-4-carboxylic acid synthesized by the method shown in Example 1, and one drop of pyridine was added. The mixture was refluxed for 6 hours. After the reaction, the reaction mixture was concentrated to obtain 4'-dodecyloxy-3'-fluorobiphenyl-4-carbonyl chloride. To the product was added 2.15 g of 4-hydroxyphenyl (s)-2-ethoxypropionate. Furthermore, 10 ml of dry pyridine was added, and the mixture was stirred at room temperature for 20 hours. After the reaction, the reaction mixture was poured into a large amount of ethyl acetate, and the mixture was washed twice with a dilute aqueous solution of hydrochloric acid, and three times with water. The ethyl acetate layer was dried over anhydrous sodium sulfate, and concentrated to give 6.05 g of crude crystals. The desired product was separated by silica gel chromatography using ethyl acetate/hexane as an eluent. Recrystallization from ethanol gave 4.01 g (yield 67%) of the desired product.

Provenance & Evidence