Paracetamol Hydrolysis question (4-aminophenol)

[Athiril]

Not after a parodinal formula.

I was wondering, how many mol to how many mol it takes for paracetamol to convert to 4-aminophenol, using potassium hydroxide.

edit: and the resulting amount of 4-aminophenol.

[gainer]

It takes 151.17 grams of paracetamol (Tylenol) to make 109.13 grams of 4-aminophenol.

[Athiril]

The important part is how much potassium hydroxide does that take? Is it 1 mol to 1 mol?

If you get less 4-aminophenol than the weight of paracetamol and hydroxide together.. what are the byproducts?

[Alan Johnson]

If you use paracetamol (insoluble) to make p-aminophenol (insoluble) how do you know the reaction has gone to completion and the result is not a mixture of the two?To get round this I make the aminophenolate which is soluble.I use sodium not potassium but the equation can be converted by replacing Na=23 by K=39.The by-products are sodium acetate and water.

C8H9NO2......+.....2NaOH...........->...C6H6NaNO....+C2H3NaO2.....+H2O
Paracetamol..Sodium Hydroxide....->.Sodium Aminophenolate...+...+..
151.17..................80...............->....131.12.......

[Kirk Keyes]

You probably want an excess of NaOH there too to drive the reaction and keep the pH up for the hydrolysis...