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Volumn 64, Issue 9, 1999, Pages 3012-3018

The reactivity of o-hydroxybenzyl alcohol and derivatives in solution at elevated temperatures

Author keywords

[No Author keywords available]

Indexed keywords

ANISOLE; ANTHRACENE DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; ETHER DERIVATIVE; LIGNIN; METHANOL; ORTHO CRESOL; PHENOL; SALIGENIN; SOLVENT; TERT BUTYL ALCOHOL;

EID: 0033617162     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981110f     Document Type: Article
Times cited : (28)

References (58)
  • 2
    • 51249170498 scopus 로고
    • ( 2) E.g.: Solár, R.; Kacik, F. Holz Roh. Werkst. 1995, 53, 123-128. Destiné, J. N.; Wang, J.; Heitner, C.; Manley, R. S. J. J. Pulp Paper Sci. 1996, 22, J24-J30. Pardini, V. L.; Vargas, R. R.; Viertler, H. Tetrahedron 1992, 48, 7221-7228. Ni, Y.; Hu, Q. J. Appl. Polym. Sci. 1995, 57, 1441-1446. Kleinert, T. Monatsh. Chem. 1952, 82, 623- 628. Wang, M.; Smith, J. M.; McCoy, B. J. Energy Fuels 1993, 7, 78-84. Sakai, K.; Takagi, T.; Imamura, H. Mok. Gak. 1990, 36, 553- 558.
    • (1995) Holz Roh. Werkst. , vol.53 , pp. 123-128
    • Solár, R.1    Kacik, F.2
  • 3
    • 0029753080 scopus 로고    scopus 로고
    • ( 2) E.g.: Solár, R.; Kacik, F. Holz Roh. Werkst. 1995, 53, 123-128. Destiné, J. N.; Wang, J.; Heitner, C.; Manley, R. S. J. J. Pulp Paper Sci. 1996, 22, J24-J30. Pardini, V. L.; Vargas, R. R.; Viertler, H. Tetrahedron 1992, 48, 7221-7228. Ni, Y.; Hu, Q. J. Appl. Polym. Sci. 1995, 57, 1441-1446. Kleinert, T. Monatsh. Chem. 1952, 82, 623- 628. Wang, M.; Smith, J. M.; McCoy, B. J. Energy Fuels 1993, 7, 78-84. Sakai, K.; Takagi, T.; Imamura, H. Mok. Gak. 1990, 36, 553- 558.
    • (1996) J. Pulp Paper Sci. , vol.22
    • Destiné, J.N.1    Wang, J.2    Heitner, C.3    Manley, R.S.J.4
  • 4
    • 0026660340 scopus 로고
    • ( 2) E.g.: Solár, R.; Kacik, F. Holz Roh. Werkst. 1995, 53, 123-128. Destiné, J. N.; Wang, J.; Heitner, C.; Manley, R. S. J. J. Pulp Paper Sci. 1996, 22, J24-J30. Pardini, V. L.; Vargas, R. R.; Viertler, H. Tetrahedron 1992, 48, 7221-7228. Ni, Y.; Hu, Q. J. Appl. Polym. Sci. 1995, 57, 1441-1446. Kleinert, T. Monatsh. Chem. 1952, 82, 623- 628. Wang, M.; Smith, J. M.; McCoy, B. J. Energy Fuels 1993, 7, 78-84. Sakai, K.; Takagi, T.; Imamura, H. Mok. Gak. 1990, 36, 553- 558.
    • (1992) Tetrahedron , vol.48 , pp. 7221-7228
    • Pardini, V.L.1    Vargas, R.R.2    Viertler, H.3
  • 5
    • 0029379050 scopus 로고
    • ( 2) E.g.: Solár, R.; Kacik, F. Holz Roh. Werkst. 1995, 53, 123-128. Destiné, J. N.; Wang, J.; Heitner, C.; Manley, R. S. J. J. Pulp Paper Sci. 1996, 22, J24-J30. Pardini, V. L.; Vargas, R. R.; Viertler, H. Tetrahedron 1992, 48, 7221-7228. Ni, Y.; Hu, Q. J. Appl. Polym. Sci. 1995, 57, 1441-1446. Kleinert, T. Monatsh. Chem. 1952, 82, 623- 628. Wang, M.; Smith, J. M.; McCoy, B. J. Energy Fuels 1993, 7, 78-84. Sakai, K.; Takagi, T.; Imamura, H. Mok. Gak. 1990, 36, 553- 558.
    • (1995) J. Appl. Polym. Sci. , vol.57 , pp. 1441-1446
    • Ni, Y.1    Hu, Q.2
  • 6
    • 0345026580 scopus 로고
    • ( 2) E.g.: Solár, R.; Kacik, F. Holz Roh. Werkst. 1995, 53, 123-128. Destiné, J. N.; Wang, J.; Heitner, C.; Manley, R. S. J. J. Pulp Paper Sci. 1996, 22, J24-J30. Pardini, V. L.; Vargas, R. R.; Viertler, H. Tetrahedron 1992, 48, 7221-7228. Ni, Y.; Hu, Q. J. Appl. Polym. Sci. 1995, 57, 1441-1446. Kleinert, T. Monatsh. Chem. 1952, 82, 623-628. Wang, M.; Smith, J. M.; McCoy, B. J. Energy Fuels 1993, 7, 78-84. Sakai, K.; Takagi, T.; Imamura, H. Mok. Gak. 1990, 36, 553- 558.
    • (1952) Monatsh. Chem. , vol.82 , pp. 623-628
    • Kleinert, T.1
  • 7
    • 0027306985 scopus 로고
    • ( 2) E.g.: Solár, R.; Kacik, F. Holz Roh. Werkst. 1995, 53, 123-128. Destiné, J. N.; Wang, J.; Heitner, C.; Manley, R. S. J. J. Pulp Paper Sci. 1996, 22, J24-J30. Pardini, V. L.; Vargas, R. R.; Viertler, H. Tetrahedron 1992, 48, 7221-7228. Ni, Y.; Hu, Q. J. Appl. Polym. Sci. 1995, 57, 1441-1446. Kleinert, T. Monatsh. Chem. 1952, 82, 623- 628. Wang, M.; Smith, J. M.; McCoy, B. J. Energy Fuels 1993, 7, 78-84. Sakai, K.; Takagi, T.; Imamura, H. Mok. Gak. 1990, 36, 553- 558.
    • (1993) Energy Fuels , vol.7 , pp. 78-84
    • Wang, M.1    Smith, J.M.2    McCoy, B.J.3
  • 8
    • 0344595574 scopus 로고
    • ( 2) E.g.: Solár, R.; Kacik, F. Holz Roh. Werkst. 1995, 53, 123-128. Destiné, J. N.; Wang, J.; Heitner, C.; Manley, R. S. J. J. Pulp Paper Sci. 1996, 22, J24-J30. Pardini, V. L.; Vargas, R. R.; Viertler, H. Tetrahedron 1992, 48, 7221-7228. Ni, Y.; Hu, Q. J. Appl. Polym. Sci. 1995, 57, 1441-1446. Kleinert, T. Monatsh. Chem. 1952, 82, 623- 628. Wang, M.; Smith, J. M.; McCoy, B. J. Energy Fuels 1993, 7, 78-84. Sakai, K.; Takagi, T.; Imamura, H. Mok. Gak. 1990, 36, 553-558.
    • (1990) Mok. Gak. , vol.36 , pp. 553-558
    • Sakai, K.1    Takagi, T.2    Imamura, H.3
  • 21
    • 0000933963 scopus 로고
    • E.g.: Sprung, M. M.; Gladstone, M. R. J. Am. Chem. Soc. 1949, 71, 2907-2913. Forrester, A. R.; Wardell, J. L. In Chemistry of Carbon Compounds, vol. IIIA, 2nd ed.; Elsevier: Amsterdam, 1971; pp 304- 305. Natesan, R.; Yeddanapalli, L. M. Ind. J. Chem. 1974, 12, 691- 694.
    • (1949) J. Am. Chem. Soc. , vol.71 , pp. 2907-2913
    • Sprung, M.M.1    Gladstone, M.R.2
  • 22
    • 0000933963 scopus 로고
    • Elsevier: Amsterdam
    • E.g.: Sprung, M. M.; Gladstone, M. R. J. Am. Chem. Soc. 1949, 71, 2907-2913. Forrester, A. R.; Wardell, J. L. In Chemistry of Carbon Compounds, vol. IIIA, 2nd ed.; Elsevier: Amsterdam, 1971; pp 304-305. Natesan, R.; Yeddanapalli, L. M. Ind. J. Chem. 1974, 12, 691- 694.
    • (1971) Chemistry of Carbon Compounds, Vol. IIIA, 2nd Ed. , vol.3 A , pp. 304-305
    • Forrester, A.R.1    Wardell, J.L.2
  • 23
    • 0000933963 scopus 로고
    • E.g.: Sprung, M. M.; Gladstone, M. R. J. Am. Chem. Soc. 1949, 71, 2907-2913. Forrester, A. R.; Wardell, J. L. In Chemistry of Carbon Compounds, vol. IIIA, 2nd ed.; Elsevier: Amsterdam, 1971; pp 304- 305. Natesan, R.; Yeddanapalli, L. M. Ind. J. Chem. 1974, 12, 691-694.
    • (1974) Ind. J. Chem. , vol.12 , pp. 691-694
    • Natesan, R.1    Yeddanapalli, L.M.2
  • 24
    • 0344595571 scopus 로고    scopus 로고
    • note
    • a values of around 4 and 10, respectively, the acidity is still dictated by the organic acid.
  • 26
    • 0345026577 scopus 로고    scopus 로고
    • note
    • 9
  • 27
    • 0344595570 scopus 로고    scopus 로고
    • note
    • olig).
  • 30
    • 0344164019 scopus 로고    scopus 로고
    • note
    • 17
  • 32
    • 0004200260 scopus 로고
    • Brooks/Cole: Pacific Grove
    • McMurry, J. Organic Chemistry, 2nd ed.; Brooks/Cole: Pacific Grove, 1988; p 596. o-HBA or acidic impurities can serve as the acid catalyst.
    • (1988) Organic Chemistry, 2nd Ed. , pp. 596
    • McMurry, J.1
  • 33
    • 0344595568 scopus 로고    scopus 로고
    • note
    • Remarkably, next to 2,2-dimethylchroman (9), another, yet unknown product, was observed when tert-butyl alcohol was used as a solvent together with methanol, 2-propanol, and benzyl alcohol.
  • 34
    • 0345457692 scopus 로고    scopus 로고
    • note
    • In phenol, 2,2′- and 2,4′-DHD (11 and 15) are identified by comparison with spectra in the NIST GC-MS library. In anisole, 2,2′- and 2,4′-HMD (12 and 16) are identified based on GC (retention times) and GC-MS analysis.
  • 37
    • 0344164018 scopus 로고    scopus 로고
    • note
    • -1.
  • 40
    • 0345457689 scopus 로고    scopus 로고
    • note
    • In these experiments, the mass balance amounted to 43-47% of the initial o-HBA concentration. In all experiments ca. 2% of the dimer of o-HBA was found and ca. 3% of an unknown, high-boiling product.
  • 41
    • 0344164017 scopus 로고    scopus 로고
    • note
    • -1.
  • 48
    • 0039316897 scopus 로고
    • Olah, G. A., Schleyer, P. v. R., Eds.; Wiley: New York
    • (a) Nenitzescu, C. D. In Carbonium Ions; Olah, G. A., Schleyer, P. v. R., Eds.; Wiley: New York, 1970; Vol. 2, pp 463-520.
    • (1970) Carbonium Ions , vol.2 , pp. 463-520
    • Nenitzescu, C.D.1
  • 52
    • 0344164016 scopus 로고    scopus 로고
    • note
    • -1, respectively.
  • 53
    • 0345026575 scopus 로고    scopus 로고
    • To be published
    • By using differential functional theory (DFT) calculated values from: Santoro, D.; Korth, H. G.; Mulder, P. To be published.
    • Santoro, D.1    Korth, H.G.2    Mulder, P.3
  • 57
    • 0344164015 scopus 로고    scopus 로고
    • note
    • The authors wish to thank an anonymous reviewer for insisting that our data are also consistent with o-QM reactivity.


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