Tetrahydrofuran → 2-(1,3,5-Triethylphenyl)-2-oxoacetic acid

Participants

Reaction Steps

To a 3 L volume four-necked flask, tetrahydrofuran (750 ml) and ethyl 2-(1,3,5-triethylphenyl)-2-oxoacetate (9-b) (261.0 g) were added, and sodium hydroxide (88 g) dissolved in water (237 g) was added dropwise thereto at about 15-20° C. The resulting mixture was stirred at room temperature for 1 hour and 30 minutes. The solid was removed by decantation. The liquid part was concentrated under reduced pressure. The residue was extracted with toluene and water. After the organic layer was removed, the aqueous layer was washed with toluene. The pH of the aqueous layer was adjusted to 1 with dilute sulfuric acid under cooling, and then the aqueous layer was extracted with toluene. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered to remove the insolubles. The filtrate was concentrated under reduced pressure to give 214.8 g of 2-(1,3,5-triethylphenyl)-2-oxoacetic acid (8-b).

Provenance & Evidence