Question

Devise a 4-step synthesis of the epoxide from benzene?

Answer 1

To synthesize an epoxide from benzene, a four-step process is used involving hydroxylation of benzene to phenol, acylation to form 2-chloroacetophenone, conversion to the oxime, and finally a Beckmann rearrangement to yield the epoxide.

Step-by-step explanation:

Four-Step Synthesis of Epoxide from Benzene

Converting benzene to an epoxide involves multiple functional group transformations. To achieve the synthesis of an epoxide from benzene, the following four-step process can be applied:

1. First, the benzene is converted into phenol by a process called hydroxylation. This can be accomplished using various reagents such as sulfuric acid and hydrogen peroxide in the so-called Cumene process.
2. Next, the phenol is reacted with chloroacetyl chloride in the presence of a base like pyridine to produce 2-chloroacetophenone.
3. The 2-chloroacetophenone is then converted into the corresponding oxime by reaction with hydroxylamine under acidic conditions.
4. Finally, the oxime is transformed into the epoxide by a Beckmann rearrangement, typically using sulfuric acid as a catalyst or other acid catalysts.

These steps provide a general pathway to transform benzene into an epoxide, though the specifics of reagents and conditions may vary depending on the desired substitution pattern of the epoxide and the yields of each step.