103-93-5

Usage

Uses

Used in Flavoring Industry:
P-TOLYL ISOBUTYRATE is used as a flavoring agent for its strong, lily-narcissus odor, adding a unique and pleasant scent to various food products and beverages. Its powerful aroma makes it a valuable ingredient in the creation of flavor profiles for a wide range of applications within the industry.

Preparation

By esterification of p-cresol with isobutyric acid.

Safety Profile

Moderately toxic by ingestion and skin contact. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C11H14O2/c1-8(2)11(12)13-10-6-4-9(3)5-7-10/h4-8H,1-3H3

Upstream product

• 106-44-5 p-cresol 
• 79-31-2 isobutyric Acid 
• 97-72-3 2-Methylpropionic anhydride 
• 79-30-1 isobutyryl chloride 

Downstream Products

• 64207-03-0 1-(2-hydroxy-5-methylphenyl)-2-methylpropan-1-one 
• 17459-72-2 p-Carboxyphenyl-2-methylpropionat 

Relevant academic research and scientific papers

C-H Functionalization via Remote Hydride Elimination: Palladium Catalyzed Dehydrogenation of ortho-Acyl Phenols to Flavonoids

Although deprotonation of electron-poor C-H bonds to carbon anions with bases has long been known and widely used in organic synthesis, the hydride elimination from electron-rich C-H bonds to carbon cations or partial carbocations for the introduction of nucleophiles is a comparatively less explored area. Here we report that the carbonyl β-C(sp3)-H bond hydrogens of ortho-acyl phenols could be substituted by intramolecular phenolic hydroxyls to form O-heterocycles, followed by dehydrogenation of the O-heterocycle into flavonoids. The cascade reaction is catalyzed by Pd/C without added oxidants and sacrificing hydrogen acceptors.

Fluorous 4-N,N-dimethylaminopyridine (DMAP) salts as simple recyclable acylation catalysts

The use of an easily accessible fluorous salt of DMAP, 1-R, as an active and recyclable acylation catalyst, under simple conditions has been reported. The recyclability of organic- and metal-based catalysts is of prime interest for the development of sustainable synthesis processes. The alcohol and the anhydride were mixed in a 10 mL round-bottomed flask and 1-R was added. The DMAP-catalyzed esterification reaction of an alcohol is performed in nonpolar solvents with an anhydride as the acyl donor, in the presence of a base in stoichiometric amounts. The simplicity of the process (readily accessible catalyst, easy to handle and to recover) makes it an attractive alternative for cleaner and safer acylation reactions, which could be used with asymmetric dialkylaminopyridines, or in other transformations, such as the Baylis Hillman reaction.

Lipase catalyzed esterification of cresols

Esters of m- and p-cresols with organic acids having carbon chain lengths C2-C18 have been prepared by using lipases from porcine pancreas and Rhizomucor miehei. Gram level conversions are carried out under non-solvent conditions in case of shake flask experiments and continuous removal of water at bench-scale levels. Addition of 0.1 mL of 0.1M phosphate buffer at pH 7.0 to the reaction mixture shows better conversions. Optimization studies have been carried out for p-cresyl laurate synthesis using Rhizomucor miehei lipase which show a maximum conversion of 74.4 %. Better conversions are obtained with larger amounts of enzyme. Porcine pancreas lipase catalyzed synthesis of m- and p-cresyl esters show that under identical reaction conditions acids with lower carbon chain lengths (C2-C4) give ester yields above 30%, while those with longer carbon chain lengths give ester yields 30%.