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Synthesis 2009(8): 1318-1322
DOI: 10.1055/s-0028-1088025
DOI: 10.1055/s-0028-1088025
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Convenient Method for Converting Hydroxyacetophenones into Their Ethylene or Trimethylene Acetals
Further Information
Received
6 November 2008
Publication Date:
25 March 2009 (online)
Publication History
Publication Date:
25 March 2009 (online)

Abstract
Various types of hydroxyacetophenones are efficiently converted into the corresponding ethylene acetals in the presence of ethane-1,2-diol, triisopropyl orthoformate, and a catalytic amount of cerium(III) trifluoromethanesulfonate under mild reaction conditions. The homologous trimethylene acetals can be also prepared in the same way.
Key words
acetal - cerium(III) trifluoromethanesulfonate - hydroxyacetophenone - Lewis acid - protecting group
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1a
Meskens FAJ. Synthesis 1981, 501 -
1b
Sandler SR.Karo W. Organic Functional Group Preparations 2nd ed., Vol. III: Academic; New York: 1989. Chap. 1. -
1c
Macpherson DT.Harshad KR. In Comprehensive Organic Functional Group Transformations Vol. 4:Katritzky AR.Meth-Cohn O.Rees CW. Pergamon; Oxford: 1995. p.159 -
1d
Kocienski PJ. Protecting Groups 3rd ed: Georg Thieme Verlag; New York: 2004. Chap. 2. -
1e
Wuts PGM.Greene TW. Greene’s Protective Groups in Organic Synthesis 4th ed.: Wiley; New York: 2007. Chap. 4. - For ethylene acetalization of acetophenone, see:
-
2a
Reddy BM.Reddy VR.Giridhar D. Synth. Commun. 2001, 31: 1819 -
2b
Kawabata T.Mizugaki T.Ebitani K.Kaneda K. Tetrahedron Lett. 2001, 42: 8329 -
2c
Firouzabadi H.Iranpoor N.Shaterian HR. Bull. Chem. Soc. Jpn. 2002, 75: 2195 -
2d
Leonard NM.Oswald MC.Freiberg DA.Nattier BA.Smith RC.Mohan RS. J. Org. Chem. 2002, 67: 5202 -
2e
Palaniappan S.Narender P.Saravanan C.Rao VJ. Synlett 2003, 1793 -
2f
Khan AT.Mondal E.Ghosh S.Islam S. Eur. J. Org. Chem. 2004, 2002 -
2g
Gregg BT.Golden KC.Quinn JF. Tetrahedron 2008, 64: 3287 - For trimethylene acetalization of acetophenone, see:
-
2h
Karimi B.Ebrahimian GR.Seradj H. Org. Lett. 1999, 1: 1737 -
2i
Firouzabadi H.Iranpoor N.Karimi B. Synlett 1999, 321 -
2j
Firouzabadi H.Iranpoor N.Karimi B. Synth. Commun. 1999, 29: 2255 -
2k
Gopinath R.Haque SJ.Patel BK. J. Org. Chem. 2002, 67: 5842 -
2l
Karimi B.Golshani B. Synthesis 2002, 784 -
2m
Karimi B.Hazarkhani H.Maleki J. Synthesis 2005, 279 - 3
Grözinger K.Hess F. Synthesis 1977, 411 - 4
Kuboki A.Yamamoto T.Ohira S. Chem. Lett. 2003, 32: 420 - 5
Ma S.Venanzi LM. Synlett 1993, 751 - 6 Zeolite HSZ-360-catalyzed ethylene
acetalization of 3-hydroxyacetophenone was reported:
Ballini R.Bosica G.Frullanti B.Maggi R.Sartori G.Schroer F. Tetrahedron Lett. 1998, 39: 1615 - For the use of Ce(OTf)3 in other types of reactions, see: for acylation:
-
7a
Dalpozzo R.De Nino A.Maiuolo L.Procopio A.Nardi M.Bartoli G.Romeo R. Tetrahedron Lett. 2003, 44: 5621 -
7b
Bartoli G.Dalpozzo R.De Nino A.Maiuolo L.Nardi M.Procopio A.Tagarelli A. Green Chem. 2004, 6: 191 -
7c
Bartoli G.De Nino A.Dalpozzo R.Maiuolo L.Nardi M.Procopio A.Tagarelli A. Lett. Org. Chem. 2005, 2: 51 - For cyclization:
-
7d
Keh CCK.Namboodiri VV.Varma RS.Li C.-J. Tetrahedron Lett. 2002, 43: 4993 - For deprotection:
-
7e
Dalpozzo R.De Nino A.Maiuolo L.Procopio A.Tagarelli A.Sindona G.Bartoli G. J. Org. Chem. 2002, 67: 9093 -
7f
Bartoli G.Dalpozzo R.De Nino A.Maiuolo L.Nardi M.Procopio A.Tagarelli A. Eur. J. Org. Chem. 2004, 2176
References
No reaction took place when the reaction was carried out in the absence of ethane-1,2-diol.
9Cyclic acetalization of normal ketones such as octan-2-one and acetophenone proceeded smoothly under similar reaction conditions.