Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2002(7): 0865-0868
DOI: 10.1055/s-2002-28519
DOI: 10.1055/s-2002-28519
PAPER
© Georg Thieme Verlag Stuttgart · New York
An Efficient Synthesis of Dimethylmaleic Anhydride [1]
Further Information
Received
24 January 2002
Publication Date:
14 May 2002 (online)
Publication History
Publication Date:
14 May 2002 (online)
Abstract
A facile three-step synthesis of dimethylmaleic anhydride (8) with 74% overall yield has been described starting from maleimide 1, via methylmaleimide 4, using two Wittig reactions followed by an alkaline hydrolysis.
Key words
maleic anhydride - maleimide, formaldehyde - condensation - alkylations - Wittig reactions
NCL Communication No. 6619.
- 2
Gill BG.James GD.Oates KV.Pattenden G. J. Chem. Soc., Perkin Trans. 1 1993, 2567 - 3 For references to the use of dimethylmaleic anhydride, see: Aldrichimica Acta 1980, 13: 53
-
4a
Mangaleswaran S.Argade NP. J. Chem. Soc., Perkin Trans. 1 2001, 1764 -
4b
Mangaleswaran S.Argade NP. J. Org. Chem. 2001, 66: 5259 -
4c
Mangaleswaran S.Argade NP. J. Chem. Soc., Perkin Trans. 1 2000, 3290 -
4d
Desai SB.Argade NP. J. Org. Chem. 1997, 62: 4862 -
5a
Branchaud BP.Slade RM. Tetrahedron Lett. 1994, 35: 4071 -
5b
Poigny S.Guyot M.Samadi M. J. Chem. Soc., Perkin Trans. 1 1997, 2175 -
5c
Poigny S.Guyot M.Samadi M. J. Org. Chem. 1998, 63: 1342 - 6
James GD.Pattenden G.Mills SD. Tetrahedron Lett. 1985, 26: 3617 - 7
Baurain R. inventors; Ger. Offen. 2 756 604, . ; Chem. Abstr. 1979, 90, 72437d - 8
Gedge DR.Pattenden G. J. Chem. Soc., Chem commun 1993, 2567 -
9a
Deshpande AM.Natu AA.Argade NP. J. Org. Chem. 1998, 63: 9557 ; and references cited therein -
9b
Deshpande AM.Natu AA.Argade NP. Synthesis 2001, 702 -
10a
Argade NP.Balasubramaniyan V. Heterocycles 2000, 53: 475 -
10b
Balasubramaniyan V.Argade NP. Tetrahedron 1989, 45: 835 - 11
Kreiser W.Janitschke L.Ernst VL.Sheldrick WS. Chem. Ber. 1979, 112: 397 - 12
Baumann M,Kvita V,Roth M, andWaterhouse JS. inventors; Swiss Patent 598 253. ; Chem. Abstr. 1978, 89, 109071n - 13
Boehner B, andBaumann M. inventors; Ger. Offen, 2 735 841. ; Chem. Abstr. 1978, 88, 152415u - 14
Ciba-Geigy . inventors; A.-G. Fr. Demande 2 400 013. ; Chem. Abstr. 1980, 92, 163836r - 15
Pichler H.Obenaus F.Franz G. Erdoel, Kohle, Erdgas, Petrochem. 1967, 20: 188 - 16
Kunichika S.Oka S.Tanaka K. Bull. Inst. Chem. Res. Kyoto Univ. 1966, 44: 221 -
17a
Shriner RL.Ford SG.Roll LJ. Org. Synth. Coll. Vol. 2 Wiley; Chichester: 1943. p.140 -
17b
Shriner RL.Ford SG.Roll LJ. Org. Synth. Coll. Vol. 2 Wiley; Chichester: 1943. p.368 -
18a
Baumann ME.Bosshard H.Breitenstein W.Rist G. Helv. Chim. Acta 1986, 69: 396 -
18b
Baumann ME.Bosshard H.Breitenstein W.Rihs G.Winkler T. Helv. Chim. Acta 1984, 67: 1897 -
18c
Baumann ME.Bosshard H. Helv. Chim. Acta 1978, 61: 2751 ; and references cited therein - 19
Pichler H,El D, andAmin Z. inventors; Ger. Offen. 2 206 713. ; Chem. Abstr. 1973, 79, 125875b - 20
Herrera A.Hoberg H. Synthesis 1981, 831 ; and references cited therein - 21
Janitschke L.Kreiser W. Synthesis 1976, 314 ; and references cited therein - 22
Hedaya E.Theodoropulos S. Tetrahedron 1968, 24: 2241 -
24a
Sheepeck JE.Liu W.Chamberlin AR. J. Org. Chem. 1997, 62: 387 -
24b
Adeboya MO.Edwards RL.Laessoe T.Maitland DJ.Whalley AJS. Liebigs Ann. Chem. 1996, 1437 -
24c
Miyagawa H.Hamada N.Sato M.Ueno T. Phytochemistry 1994, 36: 1319 - 25
Froborg J.Magnusson G.Thoren S. J. Org. Chem. 1975, 40: 122 - 26
Seki K.Sasaki T.Wano S.Haga K.Kaneko R. Phytochemistry 1995, 40: 1175
References and Notes
NCL Communication No. 6619.
23The reaction of TPP-maleic anhydride adduct with aldehydes is known to produce corresponding fulgides while TPP-methylmaleic anhydride adduct does not react with aldehydes. [4d] [22]