Thionyl chloride-benzotriazole in methylene chloride: A convenient solution for conversion of alcohols and carboxylic acids expeditiously into alkyl chlorides and acid chlorides by simple titration

Synlett

Volumn , Issue 11, 1999, Pages 1763-1765

  Chaudhari, Sachin S ^a   Akamanchi, Krishnacharya G ^a  

^a UNIVERSITY OF MUMBAI   (India)

Author keywords

Alcohols; Benzotriazole; Carboxylic acids; Chlorination; Thionyl chloride

Indexed keywords

ALCOHOL; ALKYL GROUP; BENZOTRIAZOLE DERIVATIVE; CARBOXYLIC ACID; CHLORIDE; DICHLOROMETHANE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; INFRARED SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TITRIMETRY;

EID: 0032704105     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2943     Document Type: Article

References (35)

1. a) Lee, J. B.; Nolan, T. J. Can. J. Chem. 1966, 44, 1331;
2. b) Yoshihara, M.; Eda, T.; Sakaki, K.; Maeshima, T. Synthesis 1980, 746;
3. c) Itoh, H.; Saito, T.; Oshima, K.; Nozaki, J. Bull. Chem. Soc. Jpn. 1981, 54, 1456;
4. d) Hwang, C. K.; Li, W. S.; Nicolaou, K. C. Tetrahedron Lett. 1984, 25, 2295;
5. e) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285;
6. f) Blame, G.; Gore, J.; Fournet, G. Tetrahedron Lett. 1986, 27, 1907;
7. g) Camps, F.; Gasol, V.; Guerrero, A. Synthesis 1987, 511;
8. h) Lee, J. G.; Kang, K. K. J. Org. Chem. 1988, 53, 3634;
9. i) Ioe, E. M.; Jones, C. J. Polyhedron 1992, 11, 3123.
10. a) Ottenheijm, H. C. J.; DE Man, J. H. M. Synthesis 1975, 163;
11. b) Bosshard, H. H.; Mory, R.; Schmid, M.; Zollinger, H. Helv. Chim. Acta. 1959, 42, 1653;
12. c) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1979, 32, 3037;
13. d) Cainelli, G.; Contento, M.; Manescalchi, F.; Plessi, L.; Panunzio, M. Synthesis 1983, 306 and references cited therein;
14. e) Hwang, Y. C.; Fowler, F. W. J. Org. Chem. 1985, 50, 2719;
15. f) Wolfe, S.; Godfrey, J. C.; Holdrege, C. T.; Perron, Y. G. Can. J. Chem. 1968, 46, 2549;
16. g) Masuhika, F.; Hitoshi, N. JP 92,117,344, 1992; Chem. Abstr. 1992, 117, 150719q.
17. g) Masuhika, F.; Hitoshi, N. JP 92,117,344, 1992; Chem. Abstr. 1992, 117, 150719q.
18. a) Brown, G. W., In The Chemistry of the Hydroxyl Group, Patai, S., Ed.; Interscience; London, 1971, Part 1, pp. 592-622;
19. b) Newkome, G. R.; Theriot, K. J.; Majestic, V. K.; Spruell, P. A.; Baker, G. R. J. Org. Chem. 1990, 55, 2838;
20. c) Ansell, M. F., In The Chemistry of Acyl Halides, Patai, S.; Ed.; Interscience; London, 1972, Chapter 2, pp. 35-68;
21. d) Ward, A. M. OSC, 1943, 2, 159.
22. a) Snyder, D. C. J. Org. Chem. 1995, 60, 2638;
23. b) Leonel, E.; Paugam, J. P.; Nedelec, J. Y. J. Org. Chem. 1997, 62, 7061;
24. c) Dong Soo, H.; Hyeung Ae, K. Bull. Korean Chem. Soc. 1998, 19, 1303;
25. d) Drabowicz, J.; Luczak, J.; Mikolajczyk, M. J. Org. Chem. 1998, 63, 9565;
26. e) Hiegel, G. A.; Ramirez, J.; Barr, R. K. Synth. Commun. 1999, 29, 1415;
27. f) Jang, D. O.; Park, D. J.; Kim, J. Tetrahedron Lett. 1999, 40, 5323.
28. a) See reference 1a;
29. b) Darzenes, G. Compt. Rend. 1911, 152, 1601.
30. Chaudhari, S. S.; Akamanchi, K. G. Synth. Commun. 1999, 29, 1741.
31. Bases such as pyridine, triethylamine, and imidazole react exothermically / violently with thionyl chloride at room temperature unlike benzotriazole, where dissolution is slightly endothermic
32. 2O (-0.5 g) to destroy excess reagent. The solids were filtered off. The filtrate can be used as such or the acid chloride can be recovered by removal of solvent.
33. a) Rebiere, F.; Samual, O.; Ricard, L.; Kagan, H. B. J. Org. Chem. 1991, 56, 5991.
34. 3): δ 0.8-2.1 (m, 36H), 4.3 (m, 2H, -OCH=).
35. Benzotriazole was recovered as follows: To a cooled solution of benzotriazole hydrochloride salt in water was added gradually a cold solution of 2% NaOH till pH was just neutral and precipitated benzotriazole was filtered off and dried. It was sufficiently pure (mp. 98°C) and can be reused.