
TY  - JOUR
A1  - Meisters, A 
A1  - Mole, T 
T1  - Exhaustive C-methylation of carboxylic acids by trimethylaluminium: A new route to t-butyl compounds
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1974
VL  - 27
IS  - 8
SP  - 1665
EP  - 1672
KW  - 
UR  - https://doi.org/10.1071/CH9741665 
N2  - Carboxylic acids are exhaustively C-methylated to t-butyl compounds by excess trimethylaluminium at c. 120º. Benzoic acid for example, gives t-butylbenzene. Similarly methylated are o-fluoro-, o-bromo-, and m-chloro-benzoic acids, 5-chloro-3-phenylsalicylic acid, 1-naphthoic acid, palmitic, oleic and undec-10-enoic acids. Adamantane-1-carboxylic acid gives mostly l-isopropenyladaman- tane, along with some 1-t-butyladamantane. Cinnamic acid gives mainly the allylically rearranged 2-methyl-4-phenylpent-2-ene. Triphenylacetic acid behaves atypically; 1,1,1-triphenylpropan-2-one and 3,3,3-triphenylpropyne result. 
ER  -

