Question

The so-called Wieland–Miescher ketone is a valuable starting material used in the synthesis of steroid hormones. How might you prepare it from 1,3-cyclohexanedione?

Short answer

The preparation of Wieland–Miescher ketone from 1,3-cyclohexanedione includes no. of type of reactions like alkylation, Robinson annulation, Michael reaction, and aldol condensation reaction.

Step-by-step solution

Preparation of Wieland–Miescher ketone

Preparation of Wieland–Miescher ketone from 1,3-cyclohexanedione starts with an alkylation reaction after treatment with a strong base which adds a methyl group to the compound. Then it will be followed by Robinson’s annulation and at last aldol condensation occurs.

The reaction is as follows