Hypo chlorination of safrole

[Vibrating_Lights]

Is there a procedure to make a 2hypochlorite from safrole or isosafrole?(RCH2-O-Cl). Apoun treatment with a base would yeild the ketone +Hcl?
Vl_

[Osmium]

Chlorination of alkenes in the presence of water produces the chlorohydrins (R-CHCl-CHOH-R). When basified they will produce the epoxide/glycol which can be converted to the ketone.
I'm not fat just horizontally disproportionate.

[sYnThOmAtIc]

Do you have any references one can look up for that procedure?

[Chromic]

Good luck getting this technique to work. I never got anything other than inconclusive results. The general idea is to have safrole in 10% NaOCl and slowly drip in HCl. Then isolate the chlorohydrin, treat with hydroxide in alcohol to get the epoxide, and then distill or rearrange to get the ketone.

I'm starting to get the sense that to use bleach as an oxidant, you need an appropriate catalyst.

[PrimoPyro]

using dry Ca(OCl)2 has this ever been tried? Is the HCl addition crucial to the reaction?

[Chromic]

It seems so. Bleach and alkene just sit in a biphasic mixture, happily spinning away. Maybe over many, many hours a reaction would take place? With a bit of hydrochloric acid, HOCl is formed... and hypochlorous acid is a much more active reagent than NaOCl.

[foxy2]

phase transfer catalyst

I wouldn't bother trying without one.
Those who give up essential liberties for temporary safety deserve neither liberty nor safety

[sYnThOmAtIc]

What are molar ratios one should use for the clorination(xxmol safrole, xxmole 10%hypo soln, xxmole hcl; xxmole   ?%naoh/etoh soln, xxmole chlorohydrin? Any heat applied or time allowed for conversion to chlorohydrin? Then what percent hydroxide/ethanol and how should the interaction occur to get epoxide? Afterward extract organic right to distill? Ok so this epoxide rearrangement has been verified to happen when it is distilled with out vacuum? I remember a long thread about it but I dont remember anybody getting ketone from it in any dream. This sounds about as easy and rewarding as the mdp2pol only problem is getting it to work eheh.

[Osmium]

Generate the Cl2 externally.
I'm not fat just horizontally disproportionate.

[Vibrating_Lights]

When using X₂ Is there not the chance of halogenation of the ring?  Is there need to protect the ring structure. Perhaps protect from UV Light would help minimize this. The dihalo compound would definatly need purification to seperate the ring structure substituted hydrohalohydrans.  If not then dosage level will be off in relation to the % analog compounds.
Vl_

[Chromic]

Foxy, yeah, I should have been using a PTC when I ran the experiments. If I was to do it again, that would be the way to go...