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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 32, 2002 - Issue 2
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Original Articles

SELECTIVE ACETYLATION OF ALIPHATIC HYDROXYL GROUP IN THE PRESENCE OF PHENOLIC HYDROXYL GROUP USING SILICA GEL SUPPORTED BF3 CATALYST

Biswanath Das Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
,
B. Venkataiah Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
&
P. Madhusudhan Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
Pages 249-252 | Received 25 Jul 2000, Published online: 16 Aug 2006

REFERENCES

  • Part 6 in the series Studies on Novel Synthetic Methodologies, for part 5 see Das, B.; Venkataiah B.; Synthesis 2000 (accepted). IICT Communication No. 4503.
  • Breton , G.W. 1997 . J. Org. Chem. , 62 : 8952 references cited therein
  • Das , B. , Madhusudhan , P. and Venkataiah , B. 1999 . Synlett , : 1569
  • Das , B. , Venkataiah , B. and Madhusudhan , P. 2000 . Synlett , 59
  • Wilson , K. and Clark , J.H. 1998 . J. Chem. Soc., Chem. Commun. , : 2135 references cited therein
  • Das , B. , Venkataiah , B. and Kashinatham , A. 1999 . Nat. Prod. Lett. , 13 : 293
  • The spectral and analytical data of the two unknown acetates (entry nos. 4 and 5) are given below. 3-(4-Hydroxyphenyl)propyl Acetate: Viscous mass, 1H NMR (CDCl3) : δ 7.05 (2H, d, J = 8.0 Hz), 6.73 (2H, d, J = 8.0 Hz), 4.11 (2H, t, J = 7.0 Hz), 2.62 (2H, t, J = 7.0 Hz), 2.08 (3H, s), 1.08–0.88 (2H, m); MS: m/z 194 (M+); Anal. calcd. for C11H14O3: C, 68.04; H, 7.22. Found C, 68.12; H, 7.17. 3-(3-Methoxy-4-hydroxyphenyl)-propyl Acetate: Viscous mass, 1H NMR (CDCl3) : δ 6.87 (1H, d, J = 8.0 Hz), 6.75–6.66 (2H, m), 4.13 (2H, t, J = 7.0 Hz), 3.90 (3H, s), 2.65 (2H, t, J = 7.0 Hz), 2.10 (3H, s), 1.05–0.90 (2H, m); MS: m/z 224 (M+); Anal. calcd. for C12H16O4: C, 64.29; H, 7.14. Found C, 64.21; H, 7.08.
  • da Graca Nascimento , M. , Zanotto , S.P. , Scremin , M. and Rezende , M.C. 1996 . Synth. Commun. , 26 : 2715
  • Das , B. , Takhi , M. , Kumar , H.M.S. , Srinivas , K.V.N.S. and Yadav , J.S. 1993 . Phytochemistry , 32 : 697
  • Rubinstein , I. , Goad , L.J. , Clague , A.D.H. and Mucheirn , L.J. 1976 . Phytochemistry , 15 : 195

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