Esterification of carboxylic acids with alcohols by 4-(4,6-dimethoxy- 1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride (DMTMM)

Synlett

Volumn , Issue 8, 1999, Pages 1255-1256

  Kunishima, Munetaka ^a   Morita, Jun ^a   Kawachi, Chiho ^a   Iwasaki, Fumiaki ^b   Terao, Keiji ^c   Tani, Shohei ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b TOKUYAMA CORPORATION   (Japan)

^c Wacker Chemicals East Asia Ltd   (Japan)

Author keywords

Carboxylic acids and derivatives; Condensation; Esterification; Triazines

Indexed keywords

2 PROPANOL; 4 (4,6 DIMETHOXY 1,3,5 TRIAZIN 2 YL) 4 METHYLMORPHOLINIUM CHLORIDE; 4 METHYLMORPHOLINE; ALCOHOL; ALCOHOL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; METHANOL; MORPHOLINE DERIVATIVE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ESTERIFICATION; POLYMERIZATION; STOICHIOMETRY;

EID: 0032793232     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2828     Document Type: Article

References (9)

1. For reviews on esterification, see: Ogliaruso, M.; Wolfe, J. F. The Chemistry of Functional Grou; Patai, S., Ed.; Wiley: Chichester; Suppl. B, Part 1, pp 411. Sutherland, I. O. Comprehensive Organic Chemistry; Barton, D. H. R.; Ollis, W. D., Ed.; Pergamon Press: Oxford, 1979; Vol. 2, pp 869. Sandler, S. R.; Karo, W. Organic Functional Group Preparations, Wasserman, H. H., Ed.; Academic Press: New York, 1983; Vol. 1, 2nd ed. pp 288. Mulzer, J. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 6, pp 323.
2. For reviews on esterification, see: Ogliaruso, M.; Wolfe, J. F. The Chemistry of Functional Grou; Patai, S., Ed.; Wiley: Chichester; Suppl. B, Part 1, pp 411. Sutherland, I. O. Comprehensive Organic Chemistry; Barton, D. H. R.; Ollis, W. D., Ed.; Pergamon Press: Oxford, 1979; Vol. 2, pp 869. Sandler, S. R.; Karo, W. Organic Functional Group Preparations, Wasserman, H. H., Ed.; Academic Press: New York, 1983; Vol. 1, 2nd ed. pp 288. Mulzer, J. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 6, pp 323.
3. For reviews on esterification, see: Ogliaruso, M.; Wolfe, J. F. The Chemistry of Functional Grou; Patai, S., Ed.; Wiley: Chichester; Suppl. B, Part 1, pp 411. Sutherland, I. O. Comprehensive Organic Chemistry; Barton, D. H. R.; Ollis, W. D., Ed.; Pergamon Press: Oxford, 1979; Vol. 2, pp 869. Sandler, S. R.; Karo, W. Organic Functional Group Preparations, Wasserman, H. H., Ed.; Academic Press: New York, 1983; Vol. 1, 2nd ed. pp 288. Mulzer, J. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 6, pp 323.
4. For reviews on esterification, see: Ogliaruso, M.; Wolfe, J. F. The Chemistry of Functional Grou; Patai, S., Ed.; Wiley: Chichester; Suppl. B, Part 1, pp 411. Sutherland, I. O. Comprehensive Organic Chemistry; Barton, D. H. R.; Ollis, W. D., Ed.; Pergamon Press: Oxford, 1979; Vol. 2, pp 869. Sandler, S. R.; Karo, W. Organic Functional Group Preparations, Wasserman, H. H., Ed.; Academic Press: New York, 1983; Vol. 1, 2nd ed. pp 288. Mulzer, J. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 6, pp 323.
5. Kunishima, M.; Kawachi, C.; Iwasaki, F.; Terao, K.; Tani, S. Tetrahedron Lett. in press.
6. Though Kaminski et al. also reported the formation of DMTMM, its ability as a condensing agent was found to be poor, probably due to decomposition of DMTMM by demethylation giving 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)morpholine either before or during the reaction, see: ref 2, and Kaminski, Z. J.; Paneth, P.; Rudzinski, J. J. Org. Chem. 1998, 63, 4248.
7. +).
8. Halfpenny, P. R.; Horwell, D. C.; Rees, D. C. Synthesis 1990, 517.
9. Cronin, J. S.; Ginah, F. O.; Murray, A. R.; Copp, J. D. Synth. Commun. 1996, 26, 3491.