I have seen a number of different plausible syntheses for paracetamol but they suffer from problems such poor regioselectivity of aromatic substitution (usually when nitrating phenol getting a mixture of undesired ortho and desired para). However, is the following not a plausible synthesis?...

1. Take aniline (I believe it's commercially available but can be synthesised from mononitration then reduction).
2. React with acetic anhydride to make the amide - still o,p directing and mildly activating and the directing effects are not acid sensitive as in aniline.
3. Do a friedel crafts acylation with the an acyl chloride.
4. React with hydrogen peroxide and sodium hydroxide to get paracetamol via a dakin reaction

Of course the acylation will suffer a little with regioselectivity issues but I feel like it will suffer less as the amide group is larger than a hydroxyl so favours para on steric grounds more strongly and is thus a better solution than nitration of phenol and subsequent reduction.

Nitration of Phenol then reduction and reaction with acetic anhydride is the most common hit on google so I assume it's the most common method. But what's wrong with what I have suggested?

I have seen a number of different plausible syntheses for paracetamol but they suffer from problems such poor regioselectivity of aromatic substitution (usually when nitrating phenol getting a mixture of undesired ortho and desired para). However, is the following not a plausible synthesis?

1. Take aniline (I believe it's commercially available but can be synthesised from mononitration then reduction).
2. React with acetic anhydride to make the amide — still ortho-, para-directing and mildly activating and the directing effects are not acid sensitive as in aniline.
3. Do a Friedel–Crafts acylation with the an acyl chloride.
4. React with hydrogen peroxide and sodium hydroxide to get paracetamol via a Dakin reaction.

Of course the acylation will suffer a little with regioselectivity issues but I feel like it will suffer less as the amide group is larger than a hydroxyl so favours para on steric grounds more strongly and is thus a better solution than nitration of phenol and subsequent reduction.

Nitration of phenol then reduction and reaction with acetic anhydride is the most common hit on google so I assume it's the most common method. But what's wrong with what I have suggested?