Org Prep Daily

September 24, 2006

p-Anisylmethylsulfone

Filed under: procedures — milkshake @ 10:24 pm

sulfone.gif

p-Anisylmethylsulfide 11.25g (72.94mmol) was dissolved in methanol (0.3L), Oxone solid 135g (219mmol, 6 eq. of persulfate) was added in one portion and the mixture was stirred for 3 hours. (The reaction was complete in 2 hours by HPLC). The solids were removed by filtration and washed with methanol, the filtrates were evaporated. The solid residue was re-crystallized from a mix of ethanol 100mL and water 400mL (to R.T., overnight). The crystallized product was collected by flitration, washed with water, dried by suction and on highvac. Y=11.898g (87.5%) of pearl-shiny white flakes. (A second crop could be obtained from supernatants but I was lazy).

1H(d6-DMSO, 400MHz): 7.847(app d, 8.9Hz, 2H), 7.160(app d, 8.9Hz, 2H), 3.857(s, 3H), 3.152(s, 3H)

7 Comments »

  1. Interesting, I always did this type of reaction with DMDO (oxone + acetone….). Nice to know OXONE does it by itself.

    Comment by milo — September 26, 2006 @ 11:17 am

  2. It might be that you can more accurately get the number of equivalents right with DMDO, if you have chemoselectivity problems.

    Comment by SJB — September 26, 2006 @ 1:09 pm

  3. By the way, I think I overdid it with the Oxone – I remembered vaguely that one is supposed to use 3-4 eqs of Oxone but I forgot that the MW on the Aldrich bottle is calculated for 2KHSO5.2KHSO4.K2SO4 so I endeded up using 6 equivs actualy. The rection was cleanly done in 2 h, in 30 min there was a trace of sulfoxide.

    Comment by milkshake — September 26, 2006 @ 1:26 pm

  4. In reality I think I just like making DMDO… I have a HUGE set of glassware for DMDO synthesis… 😉

    Comment by milo — September 26, 2006 @ 3:37 pm

  5. Yea, DMDO rocks but not for scale-up. The yield is below 10% th and the produced concentration of DMDO in acetone condensate is below 0.07M

    Comment by milkshake — September 26, 2006 @ 4:33 pm

  6. sir,
    i am working on preraration of DMDO but i am not succeed.
    so if u can send me process of preparaction of DMDO.
    thanking u

    Comment by jigar soni — September 17, 2008 @ 5:55 am

  7. jigar, there is a reliable DMDO procedure in Organic Syntheses, it is available online and free of charge. Link to Orgsyn is in the “Chemistry Resources” on this page.

    I have never made DMDO myself

    Comment by milkshake — September 17, 2008 @ 1:46 pm


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