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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 2
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Original Articles

The Dealkylation of Ortho-Alkoxy Aromatic Ketones and Aldehydes

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Pages 191-195 | Published online: 19 Dec 2006

References

  • McCarthy , J. R. , Moore , J. L. and Cregge , R. J. 1978 . Tet. Letts. , 52 : 5183 Hansson, C. and Wickberg, B. Synthesis, 1976, 3, 191; Olah, E. A.; Narang, S. C.; Balaram Gupta, B. G. and Malhotra, R. J. Org. Chem., 1979, 8, 1247; Bhatt, M. V. and Babu, J. R. Tet. Letts, 1984, 32, 3497; S. Anderson, Synthesis, 1985, 437
  • Ireland , R. E. and Walba , D. M. Org. Synth. , 56 44 Chou, T.; Yuan, J. and Tsao, C. J. Chem. Research (S), 1985, 18
  • Comins , D. L. , Brown , J. D. and Mantlo , N. B. 1982 . Tetrahedron Lett. , 39 : 3979 Comins, D. L. and Brown, J. D. Tetrahedron Lett., 1983, 49, 5465; Comins, D. L. and Brown, J. D. J. Org. Chem., 1984, 49, 1078
  • The preparation of 2-methoxy-6-tbutyloxybenzaldehyde was achieved by the direct formylation (DMF, n-BuLi, toluene) of 3-t-butyloxyanisole5. b p. 62–64°C, 0.5 mmHg. NMR δCDl3, 1.48 (9H, s, O-tBu), 6.50 (2H, d, d, H(3) and H(5)J = 8Hz), 7.30 (1H, dd, H(4)J = 8Hz), 10.30 (1H, s, CHO), 11.65 (1H, b, OH). IR vC = O, 1650cm−1, vOH, 2700–3600cm−1..
  • Holcombe , J. L. and Livingstone , T. 1986 . J. Org. Chem. , 51 : 11

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