THE SYNTHESIS OF METHYL 2-HYDROXY-5-METHOXY-3-METHYLBENZOATE

References

• Lindsay , A. S. and Jeskey , H. 1957 . Chem. Rev. , 57 : 583
   Web of Science ®Google Scholar
• Baine , O. , Adamson , G. F. , Barton , J. W. , Fitch , J. L. , Swayampati , D. R. and Harold , Jeskey . 1954 . J. Org. Chem. , 19 : 510 Carboxylation reactions in which potassium carbonate was used are described
   Web of Science ®Google Scholar
• Meek , W. H. and Charles Fuchsman , H. 1969 . J. Chem. Eng. Data , 14 : 388
   Web of Science ®Google Scholar
• Billespie , H. B. 1953 . Biochemical Preparations , 3 : 79
   Google Scholar
• Ansell , M. F. , Gosden , A. F. , Leslie , V. J. and Murray , R. A. 1971 . J. Chem. Soc., C , : 1401
   Google Scholar
• An alternate route involving the Friedel-Crafts acetylation of m-cresyl methyl ether to 4-methoxy-2-methylacetophenone, [C. R. Noller and Roger Adams, J. Am. Chem. Soc., 46, 1889 (1924)], followed by oxidation of the latter with m chloroperbenzoic acid and hydrolysis of the resulting acetate, to I was abandoned because a mixture of phenols was produced. This fact means that the acetylation of m-cresyl methyl ether with acetyl chloride in benzene gives a mixture of ketones. Because it seemed likely that acetylation of I under any conditions would give a mixture of ketones and not pure 4-methoxy-2-methylacetophenone, no further work on this route to I was performed. Noller and Adams used acetic anhydride in CS2 and did no work to show wheter the ketone produced (bp 3° range) in 87% yield was a single isomer. In our experience the ketone produced with acetyl chloride had a 4° range but was obviously impure as determined by our oxidation
   Google Scholar
• Elemental Analyses by Galbraith Laboratories, Knoxville, TN
   Google Scholar
• Still , I. W. J. and Snodin , D. J. 1972 . Can. J. Chem. , 50 : 1276
   Web of Science ®Google Scholar