Acetone → 3,5-Di-tert-butyl-4-hydroxybenzaldehyde

Participants

Reaction Steps

3,5-di tert.butyl-4-hydroxystyryl methyl ketone was prepared by adding a solution of 8 grams of sodium hydroxide in 100 milliliters of absolute ethanol to a mixture of 23.4 grams of 3,5-di tert.butyl-4-hydroxybenzaldehyde and 58 grams of acetone. The reaction mixture was stirred at room temperature for 14 hours and then at reflux temperature for 71/2 hours. After cooling, it was poured into 500 milliliters of water and the resulting mixture was neutralized by the addition of dilute hydrochloric acid. The sticky solid which precipitated was filtered off and mixed with petroleum ether. Filtration yielded 11 grams of unreacted 3,5-di tert.butyl-4-hydroxybenzaldehyde. From the filtrate was isolated 5.5 grams of the desired product which melted at 101° to 105° C.

Provenance & Evidence