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Volumn 70, Issue 23, 2005, Pages 9618-9621

Simple, rapid procedure for the synthesis of chloromethyl methyl ether and other chloro alkyl ethers

Author keywords

[No Author keywords available]

Indexed keywords

BYPRODUCTS; CARCINOGENS; CATALYSTS; SOLUTIONS; SYNTHESIS (CHEMICAL);

EID: 27744608616     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051344g     Document Type: Article
Times cited : (59)

References (38)
  • 1
    • 27744507729 scopus 로고    scopus 로고
    • note
    • A preliminary version of this work was presented at the 2003 National Organic Symposium, Bloomington, IN.
  • 4
    • 0028848907 scopus 로고
    • and references therein
    • For a review, see: Benneche, T. Synthesis 1995, 1 and references therein.
    • (1995) Synthesis , pp. 1
    • Benneche, T.1
  • 5
    • 0000828038 scopus 로고
    • John Wiley & Sons: New York, Collect
    • For a representative lab-scale procedure, see: Marvel, C. S.; Porter, P. K. Organic Syntheses; John Wiley & Sons: New York, 1941; Collect. Vol. I, p 377.
    • (1941) Organic Syntheses , vol.1 , pp. 377
    • Marvel, C.S.1    Porter, P.K.2
  • 6
    • 27744531526 scopus 로고
    • U.S. Patent 3,972,947
    • The majority of these processes rely on halide exchange between an acid chloride and dimethoxymethane, and typically employ elevated temperature and/or protic acid catalysis to accelerate the reaction. With HCl: (a) Weinstock, L. M.; Karady, S.; Sletzinger, M. U.S. Patent 3,972,947; Chem. Abstr. 1976, 85, 142633.
    • (1976) Chem. Abstr. , vol.85 , pp. 142633
    • Weinstock, L.M.1    Karady, S.2    Sletzinger, M.3
  • 10
    • 27744555617 scopus 로고    scopus 로고
    • WO 02/059070 A1
    • (e) Williams, A. G. WO 02/059070 A1; Chem. Abstr. 2002, 137, 124930.
    • (2002) Chem. Abstr. , vol.137 , pp. 124930
    • Williams, A.G.1
  • 16
    • 0024308309 scopus 로고
    • The carcinogenicity of MOMCl has been estimated to be greater than that of vinyl chloride; see Van Duuren, B. L. Environ. Res. 1989, 49, 143.
    • (1989) Environ. Res. , vol.49 , pp. 143
    • Van Duuren, B.L.1
  • 17
    • 0037967942 scopus 로고    scopus 로고
    • From dimethoxymethane using protic and/or Lewis acids: (a) Karimi, B.; Ma'mani, L. Tetrahedron Lett. 2003, 44, 6051.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 6051
    • Karimi, B.1    Ma'mani, L.2
  • 33
    • 27744587282 scopus 로고    scopus 로고
    • note
    • 2 is employed, 2 mol % MOMBr is present in solution. Under typical reaction conditions with 0.01 mol % or less catalyst, α-halo ethers from the halogenation exchange process cannot be detected.
  • 35
    • 27744448949 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy.
  • 36
    • 27744608508 scopus 로고    scopus 로고
    • note
    • 3 proceeds rapidly (less than 1 h) to 33% conversion, and then slows substantially, with 66% conversion after 16 h at 45 °C. In this instance, reaction endpoint monitoring is inaccurate because of the evaporative losses of the DMM and MOMCl during the extended reflux.
  • 37
    • 27744598670 scopus 로고    scopus 로고
    • note
    • The initial aqueous quench is mildly exothermic, and typically >98% of residual α-halo ether is decomposed when heat evolution has ceased, which is 5 min or less for preparative scale experiments (100 mmol scale). See Supporting Information for additional details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.