CuCl catalyzed selective oxidation of primary alcohols to carboxylic acids with tert-butyl hydroperoxide at room temperature

Tetrahedron Letters

Volumn 49, Issue 15, 2008, Pages 2457-2460

  Mannam, Sreedevi ^a   Sekar, G ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

Alcohol oxidation; Benzylic alcohols; Carboxylic acid; CuCl; Selective oxidation

Indexed keywords

ACETONITRILE; CARBOXYLIC ACID; COPPER CHLORIDE; DECANOL; OCTANOL; TERT BUTYL HYDROPEROXIDE;

ALCOHOL OXIDATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; ROOM TEMPERATURE;

EID: 40649115700     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.031     Document Type: Article

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23. 3CN for 1 h, p-methoxybenzyl alcohol was fully consumed and produced a 92% isolated yield of the corresponding carboxylic acid and n-octanol was left intact. Similarly, allylic and propargylic alcohols were selectively oxidized over aliphatic alcohols.
24. 3 and was then extracted with ethyl acetate. The aqueous layer was acidified to pH 2.0 using 2 N HCl and extracted with ethyl acetate. The organic layer was concentrated and purified using silica gel column chromatography to give p-methoxybenzoic acid (141.6 mg, 93% yield).