In situ formation of NOx and Br anion for aerobic oxidation of benzylic alcohols without transition metal

Synlett

Volumn , Issue 3, 2010, Pages 437-440

  Yang, Guanyu ^a   Wang, Wei ^a   Zhu, Weimin ^a   An, Cunbin ^a   Gao, Xinqin ^b   Song, Maoping ^a  

^a ZHENGZHOU UNIVERSITY   (China)

^b DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

2,2,6,6 tetramethylpiperidine N oxide; Alcohols; Bromate; Catalyst; Hydroxylammonium; Oxidation

Indexed keywords

2,2,6,6 TETRAMETHYLPIPERIDINE N OXIDE; BENZYL ALCOHOL; BROMINE; CARBONYL DERIVATIVE; HYDROXYLAMINE; NITROGEN OXIDE; OXIDE; OXYGEN; POTASSIUM BROMATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; OXIDATION; QUANTITATIVE ANALYSIS;

EID: 76249108083     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219202     Document Type: Article

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37. General Typical Procedure for the Oxidation The reaction was carried out in a 70 mL autoclave, and the general procedure is described typically with benzyl alcohol as follows: To a reactor were added benzyl alcohol (2 mL, 19.3 mmol), NH2OHHCl (174.8 mg, 10 mol%), KBrO3 (161.2 mg, 5 mol%), TEMPO (15.1 mg, 0.5 mol%), and CH2Cl2 (10 mL). The closed autoclave was charged with O2 to 0.3 MPa and warmed to 80 C under stirring. The pressure of O2 was kept under 0.4 MPa for 2 h. After cooled to r.t., 20 mL CH2Cl2 were added to the autoclave. Then the solution was analyzed by gas chromatography, which was conducted using an Agilent Technologies 6890N Network GC System with a flame ionization detector and a DB-1 capillary column (30 m 0.535 mm 3.0 mm).
38. General Isolation Procedure for the Oxidation Product After GC showed the reaction to be complete, the reaction mixture was diluted with CH2Cl2 and transferred into a separation funnel. The CH2Cl2 solution was washed with 15 mL of a sat. solution of Na2CO3, followed by brine. The organic layer was dried over anhyd Na2SO4, and the solvent was evaporated to yield the product without further purification.