A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids

被引:200
作者
Zhao, MZ [1 ]
Li, J [1 ]
Song, ZG [1 ]
Desmond, R [1 ]
Tschaen, DM [1 ]
Grabowski, EJJ [1 ]
Reider, PJ [1 ]
机构
[1] Merck & Co Inc, Merck Res Labs, Proc Res Dept, Rahway, NJ 07065 USA
关键词
chromium; catalysis; oxidation; alcohols;
D O I
10.1016/S0040-4039(98)00987-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel CrO3 catalyzed oxidation of primary alcohols to the carboxylic acids is reported. The oxidation proceeds smoothly with only 1-2 mol % of CrO3 and 2.5 equivalents of H5IO6 in wet MeCN to give the carboxylic acids in excellent yield. No significant racemization is observed for alcohols with adjacent chiral centers. Secondary alcohols are cleanly oxidized to ketones. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5323 / 5326
页数:4
相关论文
共 16 条
[1]  
ANELLI PL, 1987, J ORG CHEM, V52, P2559
[2]  
BOWDEN, 1946, J CEM SOC, P39
[3]  
BOWERS H, 1953, J CHEM SOC, P2548
[4]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[5]   SELECTIVE OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS WITH SODIUM-CHLORITE HYDROGEN-PEROXIDE [J].
DALCANALE, E ;
MONTANARI, F .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :567-569
[6]  
deNooy AEJ, 1996, SYNTHESIS-STUTTGART, P1153
[7]  
Hudlicky M., 1990, ACS MONOGR SER, V186
[8]   APPLICATION OF THE SWERN OXIDATION TO THE MANIPULATION OF HIGHLY REACTIVE CARBONYL-COMPOUNDS [J].
IRELAND, RE ;
NORBECK, DW .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (12) :2198-2200
[9]   PREPARATION OF CARBOXYLIC-ACIDS FROM ALDEHYDES (INCLUDING HYDROXYLATED BENZALDEHYDES) BY OXIDATION WITH CHLORITE [J].
LINDGREN, BO ;
NILSSON, T .
ACTA CHEMICA SCANDINAVICA, 1973, 27 (03) :888-890
[10]   STRUCTURE OF THE DIMETHYL SULFOXIDE OXALYL CHLORIDE REACTION-PRODUCT - OXIDATIONS OF HETEROAROMATIC AND DIVERSE ALCOHOLS TO CARBONYL-COMPOUNDS [J].
MANCUSO, AJ ;
BROWNFAIN, DS ;
SWERN, D .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4148-4151