Benzyl Alcohol from Toluene (methylbenzene)

[chem1a]

edit: i apologise if this is in the wrong spot - i was unsure if it should go in organic chem or in "your experiments" as it is both....

 

I am trying to get to Benzyl alcohol 1) for the chllenge of getting there and 2) for use as flavouring in some soaps (my next project - if anyone has any good recipees let me know) that im planning on making for xmas for peeps.

 

Anyhow the plan is to go Toluene---chlorination-->Benzyl Chloride ---Hydrolisys ---> Benzyl Alcohol (then possibly use alone or as an ester component)

 

I am wondering how long the Ca(OCL)2 chlorination is supposed to take

using equal volumes toluene:bleaching powder (or a slight excess of toluene to avoid Benzal chloride and trichloromethylbenzene formation)

 

I have tried refluxing @110 c in the presence of sunlight (from a mirror) for 1/2 an hour and ended up with a recieving flask full of toluene, the latter portion of whic came across at 140c rather than toluene's 110c bp .. this still is not the 189c i was expecting - i can only attribute the low bp to the seemingly low concentration formed (i am guessing azetropy must have played a role). The last portion was very irritating to the eyes and nasal passages (much more so that the free chlorine the comes off of bleaching powder) so i am assuming it probably is the intended compound

 

also note - the first time refluxing was attempted no uv light was used incase it led to substitution of the ring instead (are the bonds on the ring stornger than the methyl group's bonds?) - the bp of the fluid was 110c for the duration of the distillation and no irritating smell was noted

 

obviously 1./2 hour was well an truely not long enough. so my question is: does anyone know just how long this reaction is actually supposed to take and furthermore if the energy saver globes (the fluro ones) release any UV light t all (to use instead of sunlight as it is very inconvenient)

[YT2095]

be Very carefull when chlorinating methylbenzene with such things, if not done properly it will give off phosgene gas!

[chem1a]

Can you please elaborate on the conditions mentioned in "not done properly" that lead to phosgene production so i can avoid them

 

Also the extra ventilation in place to deal with liberated Chlorine gas should be enough to deal with this ww1 chem warfare agent shouldnt it ?(more specificly,"these" ww1 chem warfare agents - as both of them were used in the trench warfare) or are you recommending gas masks ?

 

also update ... with fluro lamps, a blacklight & 6 hours of refluxing toluene is still toluene - i guess there was not enough UV energy to break CL2 into Cl.

 

 

....will try again tomorrow with a UV tanning lamp