Water → HCID 88719164, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 12.0 g of 4'-(cyclohexylmethoxy)acetophenone, 5.8 g of selenium dioxide, 1.4 ml of water and 70 ml of p-dioxane was refluxed with stirring at 120° C. for 18.5 hours, cooled and filtered through diatomaceous earth, washing with p-dioxane. The combined filtrate and wash was poured into 200 ml of water cooled to 8° C. The yellow solid was collected and dried. An 8.1 g portion of sodium bisulfite was dissolved in 500 ml of water. To this was added a solution of the above solid in a mixture of 300 ml of ethanol and 100 ml of p-dioxane. The resulting mixture was filtered and the filtrate stored at 0° C. for 48 hours. The resulting solid was collected, washed twice with water, p-dioxane and absolute ethanol and then dried. This solid was added to 535 ml of 0.5N hydrochloric acid and heated with stirring at 75° C. for 8 minutes and then cooled to 10° C. The solid was collected, dissolved in hot p-dioxane, filtered and 20 ml of water added to the filtrate. The filtrate was cooled to 0° C., giving the desired product as a white solid, m.p. 118°-121° C.

Provenance & Evidence