Sodium Hydroxide → HCID 86690525, compound

Participants

Reaction Steps

In a nitrogen atmosphere, while a solution obtained by dissolving 27.5 g of Dess-Martin periodinane in 170 ml of (ultra-dehydrated) acetone is being cooled with ice water, a solution obtained by dissolving 19.5 g of (B) 1,5-bis(4-tert-butylphenyl)-penta-1,4-diyn-3-ol in 70 ml of (ultra-dehydrated) acetone is added to the above solution, followed by stirring at room temperature (23° C. to 25° C.) for 3 hours. A solution obtained by dissolving 5 g of sodium hydroxide in 25 ml of water is added to the reaction mixture, and the yellow precipitate is removed by suction filtration, and washed with acetone. The acetone filtrate is concentrated by distillation under reduced pressure, and 300 ml of ethyl acetate is poured into the obtained concentrated liquid to extract the organic substances, and the separated organic layer is washed with water. The concentrated organic layer is purified by being recrystallized sequentially from a mixed solvent of acetone and hexane and then from a mixed solvent of acetone and ethanol, thereby obtaining 16.0 g of (C) 1,5-bis(4-tert-butylphenyl)-penta-1,4-diyn-3-one. The yield of this stage is 82.5%.

Provenance & Evidence