A simple and highly practical oxidation of primary alcohols to acids mediated by 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)

Chemical and Pharmaceutical Bulletin

Volumn 51, Issue 7, 2003, Pages 888-889

  Zanka, Atsuhiko ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

2,2,6,6 tetramethyl 1 piperidinyloxy (TEMPO); Acid; Alcohol; One pot; Oxidation

Indexed keywords

ACID; ALCOHOL DERIVATIVE; PIPERIDINE DERIVATIVE; AMINE OXIDE; TEMPO;

ALCOHOL OXIDATION; ARTICLE; METHODOLOGY; QUANTITATIVE ANALYSIS; SYNTHESIS; CATALYSIS; DRUG EFFECT; METABOLISM; OXIDATION REDUCTION REACTION; PHARMACEUTICS; SPIN LABELING;

ACIDS; ALCOHOLS; CATALYSIS; CYCLIC N-OXIDES; OXIDATION-REDUCTION; SPIN LABELS; TECHNOLOGY, PHARMACEUTICAL;

EID: 1542785818     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.51.888     Document Type: Article

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14. General procedure for oxidation of alcohol: Ethyl acetate (750 ml) was added to a mixture of phenylethanol (61.1 g, 0.5 mol) and KBr in water (0.5 M, 100 ml), followed by addition of TEMPO (1.6 g, 10 mmol). A solution of 12% NaClO in water (390 g, 625 mmol) was added dropwise to the mixture over 30 min at 5°C at pH of 8.0-10.0. Stirring continued for 30 min at ambient temperature. Then, pH was adjusted to 5.0 by addition of 35% hydrochloric acid, followed by addition of 25% NaClO2 in water (227 g, 625 mmol) over 30 min maintaining the temperature of 27-33°C. Stirring continued for 3 h at ambient temperature. The product was extracted with ethyl acetate, washed with brine, followed by concentration to give 62.6 g of phenylacetic acid (92 % yield).
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