Q68. - Organic Chemistry

Question

Question: Capsaicin, the spicy component of hot peppers, can be prepared from amine X and acid chloride Y. Devise a synthesis of Y from (E)-6-methylhept-4-en-1-ol  [(CH₃)₂ CHCH=CH(CH₂)₃OH],CH₂(CO₂Et)₂ , and any required inorganic reagents.

Step-by-Step Solution

Answer

Answer

Step 1: Thionyl chloride

Thionyl chloride is used for the conversion of alcohol into alkyl chlorides. With the help of this reagent, versatile compounds are observed that could be further converted into those not converted directly from alcohol.

Step 2: Steps involved in the reaction

In the first step, (E)-6-methylhept-4-en-1-ol reacts with   to form (E)-7-bromo-2-methylhept-3-ene.

 

In the next step, it reacts with a nucleophile to form a substituted product. Further, it undergoes hydrolysis in the presence of heat to form (E)-7-methyloct-5-enoic acid.

 

In the last step, it reacts with SOCl₂  to form Y. The complete reaction is shown below:

                                                Synthesis of Y