Benzaldehyde_oxime

Benzaldehyde oxime

Benzaldehyde oxime

Chemical compound

Benzaldehyde oxime is an organic compound with the formula C7H7NO. Benzaldehyde oxime can be synthesized from benzaldehyde and hydroxylamine hydrochloride in presence of a base. The reaction at room temperature in methanol gives 9% E-isomer and 82% Z-isomer.[2]

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Reactions

Benzaldehyde oxime undergoes Beckmann rearrangement to form benzamide, catalyzed by nickel salts[3] or photocatalyzed by BODIPY.[4] Its dehydration yields benzonitrile. It can be hydrolyzed to regenerate benzaldehyde.[5]

It reacts with N-chlorosuccinimide in DMF to form benzohydroximoyl chloride, in which chlorine replaces hydrogen on the carbon attached to the nitrogen in benzaldehyde oxime.[6]

References

  1. [1]
    Karthikeyan, Parasuraman; Aswar, Sachin Arunrao; Muskawar, Prashant Narayan; Sythana, Suresh Kumar; Bhagat, Pundlik Rambhau; Kumar, Sellappan Senthil; Satvat, Pranveer S. (November 2016). "A novel l-amino acid ionic liquid for quick and highly efficient synthesis of oxime derivatives – An environmental benign approach". Arabian Journal of Chemistry. 9: S1036–S1039. doi:10.1016/j.arabjc.2011.11.007. ISSN 1878-5352.
  2. [2]
    Kim, Bo Ram; Sung, Gi Hyeon; Kim, Jeum-Jong; Yoon, Yong-Jin (20 April 2013). "A Development of Rapid, Practical and Selective Process for Preparation of Z-Oximes". Journal of the Korean Chemical Society. 57 (2): 295–299. doi:10.5012/jkcs.2013.57.2.295. ISSN 1017-2548.
  3. [3]
    Johnson, A.K.; Miller, I.D. (January 1976). "Kinetic and mechanistic studies of the rearrangement of benzaldoxime to benzamide catalysed by nickel acetate". Inorganica Chimica Acta. 16: 181–184. doi:10.1016/S0020-1693(00)91710-9. ISSN 0020-1693.
  4. [4]
    Peng, Xiaoyan; liu, Yutong; Shen, Qing; Chen, Dan; Chen, Xueqin; Fu, Yuning; Wang, Jingxia; Zhang, Xiaobin; Jiang, Hezhong; Li, Jiahong (31 August 2022). "BODIPY Photocatalyzed Beckmann Rearrangement and Hydrolysis of Oximes under Visible Light". The Journal of Organic Chemistry. 87 (18): 11958–11967. doi:10.1021/acs.joc.2c00813. eISSN 1520-6904. ISSN 0022-3263. PMID 36044674. S2CID 251979166.
  5. [5]
    Loupy, André; Régnier, Serge (August 1999). "Solvent-free microwave-assisted Beckmann rearrangement of benzaldehyde and 2-hydroxyacetophenone oximes". Tetrahedron Letters. 40 (34): 6221–6224. doi:10.1016/S0040-4039(99)01159-4. ISSN 0040-4039.
  6. [6]
    Cherney, Robert J.; Wang, Zhongyu. Preparation of 5-[3-phenyl-4-(trifluoromethyl)isoxazol-5-yl]-1,2,4-oxadiazole derivatives for treatment of autoimmune and chronic inflammatory diseases. 2012 WO 2012061459 A1.
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