A couple weeks ago i had success with making methyl salicylate (probably the easiest ester to make). It has a very pleasant sweet root beer mint lifesavers kind of smell.
so I'm currently attempting to make isopropyl salicylate, to discover if it has a similar smell.
Attempt #1, I mixed 25 mL isopropyl alcohol and 7.3 grams salicylic acid, then added 6 mL 99% sulfuric acid catalyst (a really high amount for a fischer esterificatoin). I learned that hard way that secondary alcohols do readily dehydrate to alkenes in a high concentration of acid. The mixture immediately become a purple slush that smelled like a gas station, due to propene.
Attempt #2 is in attached pic. again I used 25 mL isopropyl alcohol and 7.3 grams salicylic acid, but this time only 0.5 mL sulfuric acid (a molar ratio of 0.07 mol H2SO4 to 1 mol limiting reagant salicylic acid). Now I'm refluxing at the boiling point of isopropyl alcohol for 3 hours, and no color change, which is a good sign. But I hope it was enough H2SO4 to catalyze esterification. I'm refluxing for 3 hours and I'll find out if this worked in a couple hours.
The thing on top of the condenser is a calcium chloride drying tube to keep moisture from condensing in the inner wall of the condenser and dripping down into flask, which is bad to reaction.
so I'm currently attempting to make isopropyl salicylate, to discover if it has a similar smell.
Attempt #1, I mixed 25 mL isopropyl alcohol and 7.3 grams salicylic acid, then added 6 mL 99% sulfuric acid catalyst (a really high amount for a fischer esterificatoin). I learned that hard way that secondary alcohols do readily dehydrate to alkenes in a high concentration of acid. The mixture immediately become a purple slush that smelled like a gas station, due to propene.
Attempt #2 is in attached pic. again I used 25 mL isopropyl alcohol and 7.3 grams salicylic acid, but this time only 0.5 mL sulfuric acid (a molar ratio of 0.07 mol H2SO4 to 1 mol limiting reagant salicylic acid). Now I'm refluxing at the boiling point of isopropyl alcohol for 3 hours, and no color change, which is a good sign. But I hope it was enough H2SO4 to catalyze esterification. I'm refluxing for 3 hours and I'll find out if this worked in a couple hours.
The thing on top of the condenser is a calcium chloride drying tube to keep moisture from condensing in the inner wall of the condenser and dripping down into flask, which is bad to reaction.
