Chlorinated aspirin

[Hystrix]

Hi all. Yesterday I was trying to chlorinate the aspirin. Aspirin (3 tablets, cca 1.5 g) was ground with the pestle and the mortar and then it was added to approx. 30-35 ml of chlorine-containing bleach (I think this bleach contains at least 1 mol/l of hypochlorite). Almost immediately this mixture had darkened and started the gassing (it had resulted in covering the solution with thick layer of foam). This gas had no smell, I think it was CO2. IMO this process follows this scheme:
1. Hydrolysis of aspirin to CH3COOH and salicylic acid ('cause bleach is strong alkaline);
2. Chlorination of salicylic acid;
3. Elimination of CO2.
Therefore, I suppose my product contains a mixture of chlorophenols and probably chloroquinones. What do you think about this stuff?

[zeocrash]

hmm, bleach, is certainly a strong alkaline, but that is caused my the NaOH in there to stabilise the NaClO
IMHO this would cause the asprin to hydrolise, but instead of forming salicylic acid, the Na+ ions would react with the salicylic acid to form the sodium salt of salisylic acid, sodium salicylate the metyl group would then hydrolise to form methane IIRC, which would probably be that colourless odourless gas that is produced.
if salicylic acid had been produced, it would have caused the hypochlorite to break down into chlorine gas, but since the gas produced had no smell i'd say it wasn't chlorine
hypochlorite + acid ==> chlorine + salt + water