'phenidates other esters..glycerine? propylene glycol

[yoyoman]

I was reading about how easy it is to swap the ester on methyl/ethylphenidate. I have a bunch of ethylphenidate that was tested to be ethylphenidate but it won't dissolve in water which i find odd, but isopropylphenidate (that surely works) also doesn't seem to like water.

I'm wondering what would happen if i put some ethylphenidate in PG and added a lot of HCL (plus some water). Its got two OH groups in different spots would I end up with a mix of esters one being like isopropyl with an extra carbon link and another isopropyl like thing with an ethyl on one side and methyl on the other? would anything small enough with an -OH group attach itself?

 

[sekio]

ethylphenidate that was tested to be ethylphenidate but it won't dissolve in water which i find odd

its probably the freebase that you have then

 

[d1nach]

I wouldnt call it easy.

First you need to use a strong acid at very high conc. Danger 1
You'll likely need to heat the solution so you'd need a fume hood probably danger 2 you'd need to probably evaporate alcohols which can ignite danger 3 you'd need to figure out how to neutralize the excess strong acid and remove it 4. Prob need to use things like diethyl ether and organic solvents to remove impurities 5

Basically chemistry hard. If your interested in chemistry though I'd suggest doing no clandestine labs. Like here your asking about ether bonds. So you can find labs from colleges about making ethyl acetate and various other esters so then you have a step by step guide and safety written out clearly. You might not get anything usable out of it but if your like me you just enjoy chemistry in general

 

[d1nach]

Ester not ether getting tired over here lol. I believe your best bet would be for learning about acid catalyst formation of esters from carboxylic acids and alcohols is getting a chemistry lab made for students learning on the formation of ethyl acetate

 

[yoyoman]

Dropped a liberal amount of fumaric acid, added white vinegar later, still sits on the top. I've read about dissolving in a non polar and bubbling HCl gas...i knew the 'phenidates acted differently but didn't think they would refuse some acid throw in the water.

I have a bottle of PG i'm curious to see if it'll dissolve (got plenty to work with / waste). Then pick up the strongest HCL over the counter and add a bunch, shaking every once in a while for days. Oh forgot PG doesn't happily evaporate....could base it (and neutralize all the extra hcl into salt) then put something like naptha on top... might take a while.

Or I could try to find pure enough methanol, i read theres an easy way to get mostly just the d isomer out too. I probably won't do any of this just wondering about it.

 

[d1nach]

HCl gas is totally different then a solution of conc. HCl
HCl strong acid
HCl strong acid + h2o weak base = cl- + h3o+ (weak acid)

Propylene glycol is an alcohol like methanol. This won't work because suppose you did everything correctly you'd have esters at one or two of the hydroxyl groups on propylene glycol in addition to at the hydroxy on ethanol.

What is the point of acetic and fumaric acid? I think you may of read acetic anhydride.

Acetic anhydride is different then white vinegar

Vinegar is acetate(-) + h3o(+)

Acetic anhydride they are linked together making it much more reactive

Adding acetic acid and formic Acid increase the amount of carboxylic acids that can form esters.

Basically even if this some how worked you'd end up with methyl acetate methyl formate propylene glycol monoacetate propylene glycol diacetate propylene glycol monofurmate propylene glycol diformate propylene glycol monoacetate monofurmate propylene glycol phenidate proylene glycol diphenidate methylphenidate

Please I know you say you aren't planning on doing this I just wanted to emphasize if someone was considering it why this won't work and will probably just make you extremely sick.

 

[adder]

Obviously, any reaction with highly flammable solvents and dangerous reagents such as concentrated acids should not be undertaken by a completely amateur person, thus I'm not telling anyone to attempt this by what I'm going to write next. However, making one ester into another with a different alkoxy group is not as difficult both in theory and practice. No matter whether one carries out transesterification under acidic or basic conditions, simply an excess of an alcohol/alkoxide and desirably distilling off the side product alcohol that forms is enough to shift the equilibrium towards desired product. Only catalytic amounts of an acid are necessary, it's not boiling the reaction in concentrated acid. Similarly, a small amount of base can also catalyze the reaction if excess of alcohol is used. Anyway, with diols such as propylene glycol you'll end up with a mixture of a diester and monoesters with unknown biological properties. The reaction is feasible though if done properly, with excess propylene glycol the less substituted monoester should be the only/major product.

 

[RandomClean3]

''h3o+ (weak acid)''
Dude what? The hydronium ion is by definition a strong acid. I think you're confusing concentration with pKa

 

[d1nach]

What i mean is h3o+ is the strongest acid that can exsist in water. Certain reactions only take place without water where acids can be much much more reactive. Incould be wrong.

 

[Pomzazed]

Glycerylphenidate and Diglycerylphenidate is far too polar to exert effect, also too bulky!
They hydrolysed into ritalinic acid in vivo (which is inactive)

 

[Pomzazed]

Glycerylphenidate and Diglycerylphenidate is far too polar to exert effect, also too bulky!
They hydrolysed into ritalinic acid in vivo (which is inactive)