Could t butanol be made from citric acid by first making dimethyl citrate, followed by the complete reduction of the open carboxcilic acid, followed
by decarboxcilation?12thealchemist - 8-4-2019 at 12:24
What reducing agent do you plan to use to reduce a carboxylic acid to an alkane, or alcohol then alkane? Also, looking at the structure, you'd
probably want to form the symmetrical monoester, and decarboxylate twice, followed by reduction to the local alkane. Jackson - 8-4-2019 at 12:46
Would esterification of those two groups cause them to be selectively decarboxilated? Or are you sugesting to form the symetrical ester, followed by
reduction to the alcohol, followed by decarboxlyation, followed by reduction of the alcohol to the alkane?
Edit:
I have a route in mind. Form the dimethyl ester, then decarboxylate. Reduce the remaining carboxcylic acid to an alcohol using NaBH4 . Then tosylate
the alcohol. Reduce to the alkane using NaBH4 through nucleophilic substitution.
[Edited on 4/8/2019 by Jackson]DavidJR - 8-4-2019 at 13:44
Sodium borohydride does not reduce carboxylic acid groups. However, it can reduce the acid to the alcohol if you first form the methyl ester.
[Edited on 8-4-2019 by DavidJR]fusso - 8-4-2019 at 14:06
But how would you selectively esterify a specific carboxyl instead of making a mixture of random esters?Jackson - 8-4-2019 at 21:31
i remember seeing somewhere that the different carboxcilic acid groups have different pKa so they could react in a certain orderfusso - 8-4-2019 at 21:59
I know pKa indicate how complete the acid dissociates into H+. Does it really have anything to do with esterification equilibrium?12thealchemist - 9-4-2019 at 01:07
As I understand it, the proposed route looks something like this:
I have used a combination of sodium bicarbonate and sodium borohydride to neutralise the free acid groups without hydrolysing the ester and to reduce
the consumption of borohydride by protonation.
Edit: Picture error
[Edited on 9-4-2019 by 12thealchemist]fusso - 9-4-2019 at 16:18
@12ta some of the C in backbone is missing12thealchemist - 10-4-2019 at 00:34
If you're looking for an OTC source of t-butanol, consider instead the dietary supplement hydroxymethylbutyrate, which is just a single
decarboxylation away from t-butanol.
Was looking at the ingredients on the back of a can of lynx Africa the other day and it says contains tert butyl alcohol.citric acid seems like a long
way away to start from.
