Step-by-step procedure:
1. Protection of the amine group: The amine group in oxilofrine can be protected by reacting it with a suitable protecting group, such as a Boc group or a Fmoc group. This will prevent the amine group from reacting in subsequent steps.
2. Oxidation of the 4-hydroxy group: The 4-hydroxy group can be oxidized to a ketone group using a mild oxidizing agent, such as pyridinium chlorochromate (PCC). This will convert the 4-hydroxy group to a 4-oxo group.
3. Deprotection of the amine group: The protecting group can be removed from the amine group using a suitable deprotecting reagent, such as trifluoroacetic acid (TFA). This will regenerate the free amine group.
Resulting compound:
The resulting compound after removing the 4-hydroxy group from oxilofrine would be 4-oxooxilofrine.