Sodium Chloride → 2,4-Hexadiyn-1,6-diol bis(p-methoxybenzene sulfonate)

Participants

Reaction Steps

Fifty grams of p-methoxybenzenesulfonyl chloride was reacted, at 15° to 18° C., with 11 grams of 2,4-hexadiyn-1,6-diol in 100 ml tetrahydrofuran, while a solution of 20 grams potassium hydroxide in 180 ml water was added dropwise over a 10 minute period. The resulting exothermic reaction was cooled at 15° to 18° C. with the aid of an ice-water bath. After the addition of the potassium hydroxide solution, the solution was allowed to stir overnight at room temperature. The mixture was then poured into 500 ml cold aqueous sodium chloride solution which resulted in a yellow precipitate. The precipitate was collected by filtration, washed with water and dried. Obtained was 41.6 grams (93% yield of theory) of a yellow brown solid, melting point 120° to 122° C.

Provenance & Evidence