Author Topic: Catechol Methylation to Safrole in DMSO?  (Read 87 times)

Scarecrow

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Catechol Methylation to Safrole in DMSO?
« on: June 04, 2013, 04:36:47 PM »
Has anybody tried this procedure? I have been planning using the products for this in a nice Strike inspired performic acid oxidation to the lovely ketone.

" A solution of 110 g of catechol, 120 ml of 50% aqueous sodium hydroxide and 200 ml of DMSO was heated to 98°C and stirred at that temperature for 30 minutes. This solution at 98°C. was added over a 30 minute period to a refluxing solution of 120 ml of methylene dichloride in 300 ml of DMSO. Thereafter, the reaction mixture was stirred at reflux for 1.5 hours. Steam was then passed into the mixture to achieve steam distillation of the product. The distillate (600 ml) was extracted with 100 ml of methylene dichloride, which extract was washed once with 50 ml of water. The methylene dichloride solution was then concentrated in vacuo at 40°C to yield 119.4g of a colorless oil. Gas chromatographic analysis showed 97.5% methylenedioxybenzene. Yield 116.4g (95.4%)."

It looks far faaarrrr too easy and OTC to be the real deal, instead of passing steam into the flask surely you could flood the flask with water and steam distill that way?

Thoughts?

syn

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Re: Catechol Methylation to Safrole in DMSO?
« Reply #1 on: June 04, 2013, 10:33:34 PM »
Use the search engine here and else where and you'll see a lot of reports. Yes you could distill that way or just use a vacuum and column. This is really pointless as 1-bromo-3,4-methylenebenzene is available really cheap commercially. Not as cheap as sassafras oil though making the whole thing a little pointless unless you are just wanting to give the reactions a shot. Yes they work as stated if you do them as stated. There are numerous improvements to them too if you use the search engine you won't have problems finding them.

zgoat65

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Re: Catechol Methylation to Safrole in DMSO?
« Reply #2 on: June 06, 2013, 01:56:34 AM »
If one has ever steam distilled using external steam source then done the same distillation one-pot, one would see the difference.  External steam always wins
If you build a man a fire, he'll be warm for a day.
If you set a man on fire, he'll be warm for the rest of his life

Scarecrow

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Re: Catechol Methylation to Safrole in DMSO?
« Reply #3 on: June 06, 2013, 03:56:10 AM »
Yeah you are probably right, I am still gathering equipment to get gas generating done I need some hose an an appropriate adapter for my flask even for my HCl gas generating.