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

被引：197
|
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
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 30期
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 50 条
  • [1] Copper-catalyzed aerobic oxidation of primary alcohols to carboxylic acids
    Yu, Yibo
    Zhai, Di
    Zhou, Zhengnan
    Jiang, Sheng
    Qian, Hui
    Ma, Shengming
    [J]. CHEMICAL COMMUNICATIONS, 2023, 59 (35) : 5281 - 5284
  • [2] Carboxylic acids from primary alcohols and aldehydes by a pyridinium chlorochromate catalyzed oxidation
    Hunsen, M
    [J]. SYNTHESIS-STUTTGART, 2005, (15): : 2487 - 2490
  • [3] Oxidation of primary alcohols to carboxylic acids with sodium chlorite catalyzed by TEMPO and bleach
    Zhao, MZ
    Li, J
    Mano, E
    Song, ZG
    Tschaen, DM
    Grabowski, EJJ
    Reider, PJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07): : 2564 - 2566
  • [4] Direct Oxidation of Primary Alcohols to Carboxylic Acids
    Cherepakhin, Valeriy
    Williams, Travis J.
    [J]. SYNTHESIS-STUTTGART, 2021, 53 (06): : 1023 - 1034
  • [5] ALDEHYDES FROM PRIMARY ALCOHOLS BY OXIDATION WITH CHROMIUM TRIOXIDE - HEPTANAL
    COLLINS, JC
    HESS, WW
    [J]. ORGANIC SYNTHESES, 1988, 50-9 : 644 - 648
  • [6] Oxidation of primary alcohols to carboxylic acids with sodium chlorite catalyzed by tempo and bleach.
    Li, J
    Zhao, MZ
    Song, ZG
    Tschaen, DM
    Grabowski, EJJ
    Reider, PJ
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U133 - U133
  • [7] Selective oxidation of primary and secondary alcohols with chromium trioxide in ionic liquid
    Zheng, YF
    Du, XF
    Bao, WL
    [J]. JOURNAL OF CHEMICAL RESEARCH, 2005, (12) : 753 - 754
  • [8] OXIDATION OF ALCOHOLS WITH CHROMIUM TRIOXIDE IN HEXAMETHYLPHOSPHORIC TRIAMIDE
    CARDILLO, G
    ORENA, M
    SANDRI, S
    [J]. SYNTHESIS-STUTTGART, 1976, (06): : 394 - 396
  • [9] An improved and practical sharpless oxidation of primary alcohols to the carboxylic acids
    Prashad, M
    Lu, S
    Kim, HY
    Hu, B
    Repic, O
    Blacklock, TJ
    [J]. SYNTHETIC COMMUNICATIONS, 1999, 29 (17) : 2937 - 2942
  • [10] Selective oxidation of primary alcohols with chromium trioxide under solvent free conditions
    Lou, JD
    Xu, ZN
    [J]. TETRAHEDRON LETTERS, 2002, 43 (35) : 6095 - 6097
12345