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.
| Identifer | oai:union.ndltd.org:BGMYU2/oai:scholarsarchive.byu.edu:etd-9368 |
| Date | 18 May 1949 |
| Creators | Thorne, Chester Lawrence |
| Publisher | BYU ScholarsArchive |
| Source Sets | Brigham Young University |
| Detected Language | English |
| Type | text |
| Source | Theses and Dissertations |
| Rights | http://lib.byu.edu/about/copyright/ |
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