Hashimoto, Riichi; Hanaya, Kengo; Sugai, Takeshi; Higashibayashi, Shuhei published an article in 2022, the title of the article was 1,2-Rearrangement from o-Quinols to Multisubstituted Catechols via Retro Diels-Alder Reaction of o-Quinol Dimers.SDS of cas: 578-58-5 And the article contains the following content:
The 1,2-rearrangement of o-quinols has been a long-standing unsolved problem since 1958. Although the rearrangement is expected to be useful for syntheses of catechol derivatives, it is hampered by many competing reactions and has not been developed as a useful methodol. Here, authors succeeded in settling this problem by a first systematic thorough investigation, establishing the 1,2-rearrangement as a cascade reaction with a retro Diels-Alder reaction from o-quinol dimers. This is a useful strategy for syntheses of substituted catechols used as synthetic building blocks for bioactive compounds and material mols. o-Quinol dimers were synthesized by improved oxidative hydroxylation of substituted phenols followed by spontaneous Diels-Alder reaction. The dimers then underwent the retro Diels-Alder reaction to regenerate the o-quinols followed by 1,2-rearrangement under neutral heating conditions at an appropriate temperature depending on the migratory substituent, furnishing substituted catechols in good yields. The competing reactions such as an elimination of a substituent or α-ketol rearrangement were minimized by controlling the reaction temperature The experimental process involved the reaction of 2-Methylanisole(cas: 578-58-5).SDS of cas: 578-58-5
The Article related to quinol dimer catechol preparation regioselective, phenol hydroxylation retro diels alder rearrangement, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Alcohols and Thiols and other aspects.SDS of cas: 578-58-5
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