the color is fine. the pdcl2 dissolved in meoh will have a light brownish look, then when the benzoquinone is dissolved it will be a brownish red like you said, then as the rxn progresses within the first couple hours or so it will briefly get very very thick and very dark like a black/red and some benzoquinone will precipitate out, but just keep stirring going strong and it will dissolve back into the solution on its own. the benzoquinone wacker with meoh isn't nearly as exothermic as with dmf, it has been said that the benzoquinone / meoh wacker is fairly exothermic on the large scale but small scale it is not at all and really needs the external heat just as Methyl Man says because on smaller scale there's no considerable exothermic heat to keep everything in solution. meoh has crappy solubility with pdcl2 and benzoquinone also, unlike dmf.
you say sandstorm, that makes me think your pd and/or bq is not dissolved. be sure to get it all dissolved before starting the reaction. some may disagree because the bq will dissolve once the reaction's going and heat is being applied but why run the risk of the pd isomerizing olefin if the bq isn't dissolved well enough? like most things, patience is key. the bq is used in excess so getting it all 100% dissolved isn't going to make or break anything, swim is just saying that it's good practice to get into and your yields will thank you
1. be sure to prestir the pdcl2 for 16-24 hours in meoh
2. add the tiny bit of h2o and add your benzoquinone, stir for an hour or longer (apply a small amount of heat if necessary) to get all the benzoquinone dissolved
3. once everything is in the reaction flask that needs to be there (meoh, pdcl2, bq, tiny amount of h2o) then make sure it's all dissolved then begin addition. a slow addition over the course of 1-1.5 hours is preferred.
the solution will get darker and thicker, you might have stirring problems. swirl by hand if stirring fails. some bq will precipitate out when the solution gets real thick and tarry but the external heat (or if doing large scale, the exothermic reaction should be enough to raise the temp enough to dissolve everything) and progression of the reaction will allow it to dissolve back in. on a small scale when the exothermic heat isn't present, you need to apply external heat. otherwise lots of the bq will not dissolve properly initially and also will not dissolve after it precipitates out when the solution gets viscous/tarry, this will lead to less ketone and more iso-olefin at least in swim's experience. so some may disagree, but swim has found that high wacker yields come down to a) pure reagents and fresh bq b) good dissolution of the pd and bq c) slow addition of the olefin d) run it for the full 8 hours, the reaction is practically complete after 3 hours but for the best yields stick with 8 hours reflux after addition. so it starts out red/brown and within the first 1-2 hours you start addition it will get thick and tarry, precipitate out bq, stirring will get tough and the solution will get much darker. as it progresses the bq will dissolve back in and the solution will thin out in consistency and become less tarry. this is all within the first couple hours, the rest of the time is entirely uneventful just maintain the light reflux temp. after the rxn is done and cooled off (so you don't get a whiff of hot meoh) you can smell one of the necks. you should smell ketone. if you smell the funk of bq then that means it has precipitated and did not dissolve back in, therefor a lot of unreacted bq and a lot of iso-olefin... or if you pd wasn't dissolved well also then a lot of unreacted olefin. if, when it's cool, you smell nothing but ketone then that's a crude indicator that you're going to be happy with the results. optionally you can put the flask in the freezer overnight then gravity filter over a #101 to catch some of the precipitate, you can gravity filter over a #102 to catch even more but it will take longer. swim has even gravity filtered over a #103 once before and it caught a TON because the 103 will catch lots of the quinone but this is not necessary, using a 102 or 103 is not necessary as the NaOH washes will get all the quinone anyway. then when swim hit the solution with the hcl it released a nice red oil instead of the typical chunk of tar that happens when you don't gravity filter at all. but in all honesty the tar is workable even though it's messy. swim recommends freezer then gravity filter over an unbleached coffee filter or 101 as a happy medium because doing a 102 or 103 is going to take FOREVER and is not worth the lack of tar. extract with solvent of choice. dcm is the best at entirely dissolving the tar, but toluene works well too and will also dissolve the tar just not quite as readily but good enough. the dcm looks cleaner after the washes than toluene does, toluene gives a black ketone that leaves yellow streaks when swirled, but it doesn't matter cuz both are inevitably vac distilled to their typical yellow glory. anyway after extraction, wash 5 x 5% refrigerator chilled NaOH, then saturated brine x 2, dry, distill. like moriarty says, screw the bicarb washes, honestly unless you enjoy emulsions and frog eggs.
