Sciencemadness Discussion Board

The Condensation Reaction Of Salicylic Acid And Acetone

SimpleChemist-238 - 10-11-2014 at 18:50

Based on some information on the web ( I do no yet have a text book) a condensation reaction is the joining of two molecules to form a new compound using a acid catalyst and forming water. Is this correct and if so what are the conditions required? (My source , http://en.wikipedia.org/wiki/Condensation_reaction )

If so can Bis-Salysilic Acid-A (Similar to BPA) be created from the reaction of salicylic acid and acetone? Also does any one have a good text book online that they could recommend?

AvBaeyer - 10-11-2014 at 19:12

Here is information on the compound you will get with some references:

Registry Number: 1433-61-0



Formula: C10 H10 O3

CA Index Name: 4H-1,3-Benzodioxin-4-one, 2,2-dimethyl-

Property Value Condition Note
Boiling Point 112-114 °C Press: 4 Torr (1) CAS
Melting Point 61 °C (2) CAS
Melting Point 58-59 °C (1) CAS

Notes:
(1) Mowry, David T.; Journal of the American Chemical Society 1947, V69, P2358-61
(2) Ziegler, E.; Monatshefte fuer Chemie 1964, V95(4-5), P1053-6

Unfortunately the structure did not paste. Google the registry/CAS number and you will get the structure.

AvB

SimpleChemist-238 - 10-11-2014 at 19:23

Is this the compound that would be the product of the reaction of salicylic acid and acetone? Any idea of how the reaction would be carried out?

DraconicAcid - 10-11-2014 at 20:32

Quote: Originally posted by SimpleChemist-238  
Based on some information on the web ( I do no yet have a text book) a condensation reaction is the joining of two molecules to form a new compound using a acid catalyst and forming water. Is this correct and if so what are the conditions required? (My source , http://en.wikipedia.org/wiki/Condensation_reaction )

If so can Bis-Salysilic Acid-A (Similar to BPA) be created from the reaction of salicylic acid and acetone? Also does any one have a good text book online that they could recommend?


Amines and alcohols will condense with acids to give amides and esters, respectively, but I'm not aware of ketones condensing with them. Do you have a cite for a more specific reaction?

SimpleChemist-238 - 11-11-2014 at 06:46

Bisphenol A was first synthesized by the Russian chemist A.P. Dianin in 1891.[13][14] This compound is synthesized by the condensation of acetone (hence the suffix A in the name)[15] with two equivalents of phenol. The reaction is catalyzed by a strong acid, such as hydrochloric acid (HCl) or a sulfonated polystyrene resin. Industrially, a large excess of phenol is used to ensure full condensation; the product mixture of the cumene process (acetone and phenol) may also be used as starting material:[7]


Source; http://en.wikipedia.org/wiki/Bisphenol_A


[img]http://en.wikipedia.org/wiki/Bisphenol_A#mediaviewer/File:Synthesis_Bisphenol_A.svg[/img]

[Edited on 11-11-2014 by SimpleChemist-238]

Nicodem - 11-11-2014 at 10:28

The synthesis of 5,5'-isopropylidenedisalicylic acid by the condensation of salicylic acid with acetone is described in DOI: 10.1021/jm00327a035. All other syntheses in the literature use the Kolbe-Schmitt reaction on bisphenol A to obtain the product.

Please post beginnings questions or literature search requests in the Beginnings section. Also, see the forum guidelines on how to do literature work by yourself.

AvBaeyer - 11-11-2014 at 20:09


Here is a file from a brief SciFinder search regarding the reaction of acetone with salicylic acid under acidic conditions. The product is that which I referred to in my original post and is different form what you apparently wanted. However, Nicodem has pointed you in your desired direction.

In any event, have a look.

AvB

Attachment: Salicyclic acid derivatives.doc (38kB)
This file has been downloaded 967 times

kmno4 - 12-11-2014 at 01:48

Quote: Originally posted by AvBaeyer  

Here is a file from a brief SciFinder search regarding the reaction of acetone with salicylic acid under acidic conditions. The product is that which I referred to in my original post and is different form what you apparently wanted.

I have had a look at your SF informations and it seems that you have not done this. There are no informations about "reaction of acetone with salicylic acid under acidic conditions" in this document.
Paper mentioned by Nicodem describes reaction of acetone, sal. acid and 60% H2SO4 (very similar is reaction with formaline, giving methylene- instead of isopropylidene- derivative). Prepared substance has mp 288 C and is different from 2,2-Dimethyl-4-keto-1,3-benzodioxane, prepared from isopropenyl acetate and sal. acid. (mp 59 C)

Nicodem - 12-11-2014 at 06:02

Quote: Originally posted by kmno4  
I have had a look at your SF informations and it seems that you have not done this. There are no informations about "reaction of acetone with salicylic acid under acidic conditions" in this document.

I checked the JACS, 69, 2358 article (first CA from the SciFinder output) and it indeed does not mention the direct condensation of salicylic acid with acetone to give the acetonide (it describes the acetonide formation using isopropenyl acetate instead).
However, the abstract of the Japonese patent does says: "A mixt. of salicylic acid 5 g, acetic anhydride 4.4 mL, and acetone 11.6 mL, and a catalytic amt. of sulfuric acid was stirred at 0° for 15 h to give the corresponding 1,3-dioxan-4-one deriv. 3.67 g (57% yield)." Activation with acetic anhydride is used in this case, and isopropenyl acetate is known to form from acetone and acetic anhydride with acid catalysis. So it is probably not a trivial matter to form the salicylic acid acetonide with unactivated acetone directly. Anyway, SimpleChemist-238 does not want the acetonide.