Successful preparation of isopropyl salicylate fragrant ester, inspired by methyl salicylate
Reference: doug's lab methyl salicylate video https://www.youtube.com/watch?v=vvrfHS4DRoM
To a round bottom flask in an ice water bath (to prevent dehydration of isopropyl alcohol to propene), I added these 2 chemicals:
>13.80 grams / 0.1 moles salicylic acid (mole ratio 1)
>28.40 mL / 0.371 moles isopropyl alcohol (mole ratio 3.7)
Then added 1 mL per minute while stirring: 5 mL / 0.0933 moles sulfuric acid (mole ratio 0.933)
I refluxed for 1.5 hours. Only 20 minutes in, I noticed the distinct smell of isopropyl salicylate coming out of the drying tube.
Once the mixture cooled down, a lot of unreacted salicylic acid precipitated out. I filtered out the unreacted salicylic acid.
after adding an arbitrary amount of saturated sodium bicarbonate solution to the filtrate, I was ecstatic to see an oily layer form on top of the aqueous layer. I collected the top layer, and did one more sodium bicarbonate wash.
I collected the crude isopropyl salicylate in a vial, to add to my collection of fragrant esters.
It smells very different from methyl salicylate.
Methyl salicylate odor: sweet, wintergreen, root beer, mint lifesavers
isopropyl salicylate is not sweet at all, not as pleasant, but still smells nice. It's vegetal, green, spinach, limey, floral, herbal. I would definitely make a candle out of this.
Reference: doug's lab methyl salicylate video https://www.youtube.com/watch?v=vvrfHS4DRoM
To a round bottom flask in an ice water bath (to prevent dehydration of isopropyl alcohol to propene), I added these 2 chemicals:
>13.80 grams / 0.1 moles salicylic acid (mole ratio 1)
>28.40 mL / 0.371 moles isopropyl alcohol (mole ratio 3.7)
Then added 1 mL per minute while stirring: 5 mL / 0.0933 moles sulfuric acid (mole ratio 0.933)
I refluxed for 1.5 hours. Only 20 minutes in, I noticed the distinct smell of isopropyl salicylate coming out of the drying tube.
Once the mixture cooled down, a lot of unreacted salicylic acid precipitated out. I filtered out the unreacted salicylic acid.
after adding an arbitrary amount of saturated sodium bicarbonate solution to the filtrate, I was ecstatic to see an oily layer form on top of the aqueous layer. I collected the top layer, and did one more sodium bicarbonate wash.
I collected the crude isopropyl salicylate in a vial, to add to my collection of fragrant esters.
It smells very different from methyl salicylate.
Methyl salicylate odor: sweet, wintergreen, root beer, mint lifesavers
isopropyl salicylate is not sweet at all, not as pleasant, but still smells nice. It's vegetal, green, spinach, limey, floral, herbal. I would definitely make a candle out of this.
