The preparation of m-alkylphenols :|bmechanisms and reactions
Work with m-alkylphenols as precursors for curare-like drugs and bactericidal agents has created an interest in the synthesis of m-alkylphenols. Syntheses of m-alkylphenols have consisted of numerous steps resulting in the production of the m-alkylphenol in very low yield. The general methods of syntheses of o-and p-alkylphenols are not applicable to m-alkylphenols. Knoevenagel, in 1874, prepared m-cresol from 3-methylcyclohexen-2-one-1 with a very poor yield. The production of m-alkylphenols from 3-alkylcyclohexen-2-one-1's has been investigated several times since then. In this work, resorcinol was hydrogenated to form cyclohexandione-1,3, which was in turn brominated to form 2-bromocyclohexandione-1,3. The 2-bromocyclohexandione-1,3 was reacted with an alkylmagnesium bromide to form a 3-alkyl-2-bromocyclohexen-2-one-1, which on pyrolysis yielded the corresponding m-alkylphenol. This procedure was followed to prepare m-ethylphenol, m-isopropylphenol, m-(n-butyl)phenol, m-cyclohexylphenol, and m-(n-dodecyl)phenol. 3-Ethylcyclohexanone was made by reduction of 3-ethylcyclohexen-2-one-1 formed from the reaction of ethyl-magnesium bromide and cyclohexandione-1,3. m-(n-Dodecyl)phenol has never been reported in the literature of chemistry, The possibility of preparing many other unreported or unaccessible compounds by modification of the procedures considered was noted.
College and Department
Physical and Mathematical Sciences; Chemistry and Biochemistry
BYU ScholarsArchive Citation
Thorne, Chester Lawrence, "The preparation of m-alkylphenols :|bmechanisms and reactions" (1949). Theses and Dissertations. 8368.