Abstract
A variety of alcohols are acetylated and formylated efficiently with acetic acid and ethyl formate in the presence of catalytic amounts of Bi(III) salts such as BiCl3, Bi(TFA)3 and Bi(OTf)3. BiCl3 and Bi(OTf)3 are also effective catalysts for acetylation of phenols. All of these catalysts are ineffective in formylation of phenols. Selective acetylation and formylation of alcohols in the presence of phenols is an additional advantage of this procedure.
Keywords
References
1.
Vogel's
, Text Book of Practical Organic Chemistry , Longman Group Ltd. , 4th edn, 1987 , pp. 501 –515 .
2.
Takahashi K.
,
Shibagaki M.
, and
Matsushita H.
, Bull. Chem. Soc. Jpn. , 1989 , 62 , 2353 .
3.
Iranpoor N.
,
Firouzabadi H.
, and
Zolfigol M. A.
, Synth. Commun. , 1998 , 28 , 1923 .
4.
Iranpoor N.
, and
Shekarriz M.
, Bull. Chem. Soc. Jpn. , 1999 , 72 , 455 .
5.
Narender N.
,
Srinivasu P.
,
Kulkarni S. J.
, and
Raghavan K. V.
, Synth. Commun. , 2000 , 30 , 1887 .
6.
Saravanan P.
, and
Singh V. K.
, Tetrahedron Lett. , 1999 , 40 , 2611 .
7.
Manohar B.
,
Reddy V. R.
, and
Reddy B. M.
, Synth. Commun. , 1998 , 28 , 3183 .
8.
Nascimento M. da G.
,
Zanotto S. P.
,
Scremin M.
, and
Rezende M. C.
, Synth. Commun. , 1996 , 26 , 2715 .
9.
Ogawa H.
,
Amano M.
, and
Chilara T.
, Chem. Commun. , 1998 , 495 .
10.
Ishihara K.
,
Kubota M.
,
Kurihara H.
, and
Yamamoto H.
, J. Org. Chem. , 1996 , 61 , 4560 .
11.
Borah R.
,
Deka N.
, and
Sarma J. C.
, J. Chem. Res(S) , 1997 , 110 .
12.
Jin T.-S.
,
Ma Y.-R.
,
Zhang Z.-H.
, and
Li T.-S.
, Synth. Commun. , 1998 , 28 , 3173 .
13.
Chauhan K.K.
,
Frost C. G.
,
Love I.
, and
Waite D.
, Synlett , 1999 , 1743 .
14.
Pansare S.V.
,
Malusare M. G.
, and
Rai A. N.
, Synth. Commun. , 2000 , 30 , 2587 .
15.
Ringold H.J.
,
Loeken B.
,
Rosenkranz G.
, and
Sondheimer F.
, J. Am. Chem. Soc. , 1956 , 78 , 816 .
16.
McOmie J. F. W.
, Protective Groups in Organic Chemistry , Plenum Press , London , 1973 , pp. 111 –112 .
17.
Caputo R.
,
Ferreri C.
, and
Palumbo G.
, Synth. Commun. , 1987 , 17 , 1629 .
18.
Barluenga J.
,
Campos P. J.
,
Gonzalez-Nunez E.
, and
Asensio G.
, Synthesis , 1985 , 426 .
19.
Fernandez I.
,
Garica B.
,
Munoz S.
,
Pedro J. R.
, and
Salud R.
, Synlett , 1993 , 489 .
20.
Deutsch J.
, and
Niclas H.-J.
, Synth. Commun. , 1993 , 23 , 1561 .
21.
Kashima C.
,
Arao H.
,
Hibi S.
, and
Omote Y.
, Tetrahedron Lett. , 1989 , 30 , 1561 .
22.
Katritzky A.R.
,
Chang H.-X.
, and
Yang B.
, Synthesis , 1995 , 503 .
23.
Gramain J.C.
, and
Remuson R.
, Synthesis , 1982 , 264 .
24.
Neveux M.
,
Bruneau C.
, and
Dixneuf P. H.
, J. Chem. Soc., Perkin Trans 1 , 1991 , 1197 .
25.
Staab H.A.
, and
Polenski B.
, Liebigs Ann. Chem. , 1962 , 655 , 95 .
26.
(a)
Effenberger F.
,
Muck A. O.
, and
Bessey E.
, Chem. Ber. , 1980 , 113 , 2086 .
27.
Effenberger F.
, and
Bessey E.
, Chem. Ber. , 1980 , 113 , 2100 .
28.
Effenberger F.
,
Keil M.
, and
Bessey E.
, Chem. Ber. , 1980 , 113 , 2110 .
29.
(a)
Mohammadpoor-Baltork I.
, and
Aliyan H.
, Synth. Commun. , 1998 , 28 , 3943 .
30.
Mohammadpoor-Baltork I.
, and
Aliyan H.
, Synth. Commun. , 1999 , 29 , 2741 .
31.
Mohammadpoor-Baltork I.
,
Tangestaninejad S.
,
Aliyan H.
, and
Mirkhani V.
, Synth. Commun. , 2000 , 30 , 2365 .
32.
(a)
Garner C.D.
, and
Hughes B.
, Advances in Inorganic Chemistry and Radiochemistry , Vol. 17 , Academic Press : New York , 1975 .
33.
Singh S.
, and
Verma A. R. D.
, Indian J. Chem. , 1983 , 22A , 814 .
34.Beilsteins Handbuch der Organischen Chemie , Spinger Verlag , 1923 , Band VI, pp. 449 .