SWIM made an absent minded mistake in a dream which is still in process. SWIM is dreaming about the conversion of 4-fluorobenzaldehyde to the corresponding phenylacetone using the darzen condensation, primarily based on the procedures posted by Barium. Here's the dilema, any quick replies of advice would bee greatly appreciated.
SWIM dissolved the proper amount of freshly cut sodium metal in anhydrous methanol to prepare a solution of sodium methoxide. Meanwhile, a mixture of methanol, the benzaldehyde, and methyl 2-chloropropionate were stirred in a 3 neck RBF fitted w/addition funnel and thermometer. SWIM's stupid error was using 0.864ml of benzaldehyde instead of the proper 8.64ml. A very absent-minded mistake. So, SWIM charged the addition funnel w/the methoxide solution, and began adding slowly, maintaining the temp under 15C. After about half the methoxide solution had added, the reaction mixture became white (it was previously clear), as if a suspension or colloid had formed. After the methoxide solution was fully added, the ice bath was removed and SWIM let it warm up to room temp.
Then SWIM realized the absent minded mistake, panicked and added the remaining 7.78ml 4-fluorobenzaldehyde in hopes the reaction may still work.
SWIM's concern is that, without the more reactive benzaldehyde around, the anion from the reaction between the methoxide and haloester may react with more haloester (the haloester was supposed to be present in roughly 0.5molar excess to the benzaldehyde) forming a byproduct and essentially making the later addition of the benzaldehyde pointless. The remaining benzaldehyde was added about 30 minutes or so after the methoxide solution was added, which took about 20 minutes itself, so about 50 minutes afterthe very beginning of the reaction.
Do any bees think the reaction may still work, are SIWM's concerns about the haloester anion reaction with other haloester unfounded?
Thanks, your urgent response appreciated!!
-SpicyBrown