Question 20.37: Outline the steps required to convert p-ethylanisole into ea......
Outline the steps required to convert p-ethylanisole into each of the following compounds.
(a) p-methoxybenzoic acid (b) 2-(p-methoxyphenyl)propanoic acid (c) 3-(p-methoxyphenyl)butanoic acid
(a) Oxidize the ethyl group to a carboxylic acid using a strong oxidizing agent such as potassium permanganate.
(b) Use NBS to prepare the secondary bromo compound of the ethyl side chain. Then, prepare the Grignard reagent using magnesium and ether. Third, add it to carbon dioxide, followed by acidification in workup.
(c) Use NBS to prepare the secondary bromo compound of the ethyl side chain. Second, prepare the Grignard reagent using magnesium and ether; third, add it to ethylene oxide to give 3-(p-methoxyphenyl)butanol. Oxidize the alcohol using the Jones reagent.