An efficient synthesis of phenol via CuI/8-hydroxyquinoline-catalyzed hydroxylation of aryl halides and potassium hydroxide

Synlett

Volumn , Issue 6, 2010, Pages 976-978

  Maurer, Stefan ^a   Liu, Wei ^b   Zhang, Xiaojing ^b   Jiang, Yongwen ^a   Ma, Dawei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

8 hydroxyquinoline; Coupling; Hydroxylation; Phenols

Indexed keywords

ARYL HALOGENIDE; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM HYDROXIDE; QUINOLINOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG HYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77949905060     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219548     Document Type: Article

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23. Typical Procedure for Preparation of 2a An oven-dried Schlenk tube was charged with CuI (19 mg, 0.1 mmol), 4-iodoanisole (1 mmol), 8-hydroxyquinoline (29 mg, 0.2 mmol), and KOH (224 mg, 4 mmol). The tube was evacuated and backfilled with argon, and DMSO (1 mL), t-BuOH (1 mL), and H2O (0.1 mL) were added. The reaction mixture was stirred at 100 C till the material was completely converted (monitored by TLC). Then the mixture was acidified to pH ~1 with 1 N HCl. Extract workup followed by chromatography afford 4-methoxyphenol in 96% yield.