Alyx Woodward (obsolete) @Alyx@computerfairi.es

well that's a fun one. looks like they're doing this all under nitrogen. probably just as well; some of the intermediates in this whole process must reek like nobody's business. plain unsubstituted thiophenol is famously stinky, being compared to the odor of burning tires, only...stronger. guessing that thiophenol is formed from vulcanized rubbers in combustion

(cont'd) and this ester, on prolonged heating with methanolic potassium hydroxide, rearranges and hydrolyzes to the thiophenol without, somewhat to my surprise, hydrolyzing the cyano group. this reaction has a name, the Newman-Kwart reaction: https://en.wikipedia.org/wiki/Newman%E2%80%93Kwart_rearrangement

then mild oxidation of the thiophenol with 30% hydrogen peroxide and anhydrous zirconium (??) chloride in acetonitrile yields the sulfonyl chloride. I believe there are other protocols for this

it's the phenol to thiophenol conversion that's the really fascinating step here, because that's not an ordinary sort of aromatic substitution. I think that it can be done with brute-force conditions on simple substrates: one obtains thiophenol from phenol by distilling with phosphorus(V) sulfide, I believe, and the yield is probably low (and the reaction smelly and dangerous)

but here, the phenol is converted to a dimethylthiocarbamate ester with dimethylthiocarbamoyl chloride (cont'd)

ok, let's do an _Organic Syntheses_ roulette

and the number is...818

I had to go to the third hit to find one that I don't remember doing some earlier time, haha

well it's a curious one. conversion of a phenol to a arylsulfonyl chloride

http://orgsyn.org/demo.aspx?prep=v94p0198

in this case the starting phenol is 4-cyanoguaiacol, the monomethyl ether of catechol only with a -CN group stuck para to the phenolic -OH

the -OH is first converted to -SH through a curious rearrangement, then oxidized to -SO₂Cl

@avi modern-day punk is so much cooler now anyway

anyway, Lomax has "things to do". they ride a bus to a place called "King's Park"

apparently there's some kind of archaeological site west of the town of "Silverdalen" (again, that's just an odd name to me, and reminiscent of Silverdale, WA) and the body was found there. no sign of physical trauma

Lomax suggests the news is almost teasing people into checking out the site for themselves. "don't do that," says dad from the couch. Lomax is on edge and wonders to themself why dad would even bring the idea up. "I've never been a troublemaker."

bleh

whatever else is true, I gotta keep going forward through this. if nothing else it's breaking us of the long-standing habit of never reading comics for more than a little bit before dropping them. maybe we actually stand a chance of getting through "Gunnerkrigg Court", after all this is done, whatever "this" even is

okay, the thirty-ninth step

https://www.parallaxcomic.com/comic/page-39

oof, the TV news is bad. a seven-year-old (seven!) girl has been found dead

what the hell has been going on

o-kay

dad says something about Lomax missing their favorite show

"what's it called? 'Anthrax'?" says mom

"Panthrax", Lomax corrects. they're clearly put out by having missed it, whatever it is

porridge (porridge?? not oatmeal? who literally eats porridge these days) is served

and everyone shushes everyone else to listen to some news bulletin

and we cut...to breakfast

ugh

page thirty-eight

https://www.parallaxcomic.com/comic/page-38

Lomax looks as they did before, red shirt, brown hair. they also look completely wasted

mom greets them in customary fashion. Lomax is sick and hungover and is barely keeping up with the morning routine

finally, a good look at dad. young-looking guy, with a moustache

mom is worried. "you don't have a fever do you?"