The day before yesterday, SwiN was reading interesting things in the library. They said "you can't directly methoxylate p-dichlorobenzene under normal pressure and temperature conditions, except maybe photochemically"...
SwiN didn't like these words, as SwiN had some big dreams for SwiN's little tin of moth crystals. Now, for SwiN's purposes, even a 10% yield of 1,4 dimethoxybenzene from moth flakes would be most acceptable. So SwiN got thinking...why do these stupid chlorines just not want to react? And the answer in SwiN's head was...because they aren't STIMULATED enough yet. Which takes light. Or heat. Or...or...sonication! Yes! Amongst other papers, SwiN has seen several, usually related to sewage cleanup, that speak of knocking chlorines off benzene rings (to be replaced with hydroxyls...), with ultrasound. And how about that, SwiN just happens to have a little baby jewelry cleaner, and boy, it could use some cleaning. So,yesterday, SwiN plopped in the sonicator:
a dollop of p-dichlorobenzene (40mmol),
a bigger spoon of NaOH (120 mmol),
a pinch of Ajax (detergent and bleach),
1g of root-killer (CuSO4 crystals),
some copper electrical wire,
2g of Oxy-clean,
a bit of the jewelry cleaner's fluid(which SwiN assumes is just soap)
100mL H2O
150mL denatured alcohol
a blob of acetone to stir things up
.... well, wouldn't you know it, but it fizzed up real nice.
And gave off a most repulsive moth-crystal-y scent. And made annoying, loud, headache-inducing ultrasonic crackling.
But then, something happened. About 30 minutes in, the tone changed, and the white foaming liquid suddenly changed brown. SwiN let it run for a while longer, then poured it out into a beaker to look. All the crystals were gone. The beaker had a nasty brown powdery gunk on the bottom, and the solution was brown, too.
A quick check indicated that hydroquinone oxidises brown in basic solution (!) Mission Successful! Sort of! There sure was nothing else in there that was brown! All white powders here! What has SwiN oxidized SwiN's stupid moth crystals into? Hydroquinone, one step away from the holy precursor of joy? Or mixed up brown crap? Maybe both? Maybe SwiN should go easy on the oxy-clean next time? But basic solution is necesary to this process!
Swin dreams of the future--a melt phase methylation?
Perhaps the moth crystals can be put in a tube with solid NaOH and a high-melting methylating agent and heated to about 170 degrees celsius. As soon as the NaOH takes a Cl and gives an OH, the methylating agent will methylate it safely to -O-Me, where it will be unaffected by the basic surroundings. Maybe.....
Any ideas, bees? What should SwiN do next with the hungry sonicator and moth flakes? Of course NaOMe comes to mind, but for some reason SwiN is having trouble finding methanol and quicklime. Sad, sad, sad.
