Hydrogen Chloride†
Gary W. Breton
University of North Carolina, Chapel Hill, NC, USA
Search for more papers by this authorPaul J. Kropp
University of North Carolina, Chapel Hill, NC, USA
Search for more papers by this authorGary W. Breton
University of North Carolina, Chapel Hill, NC, USA
Search for more papers by this authorPaul J. Kropp
University of North Carolina, Chapel Hill, NC, USA
Search for more papers by this authorAbstract
[7647-01-0] ClH (MW 36.46)
InChI = 1S/ClH/h1H
InChIKey = VEXZGXHMUGYJMC-UHFFFAOYSA-N
(reagent for hydrochlorination of alkenes and alkynes;4 cleaves epoxides1b and ethers;21a converts alcohols to chlorides12b and diols to cyclic ethers;17 chloroalkylates arenes;22 converts aldehydes to α-chloro ethers23b)
Alternate Name: Hydrochloric Acid
Solubility: sol most organic solvents.2
Form Supplied in: widely available; compressed gas; 1 M solution in AcOH, Et2O, or Me2S; 4 M solution in dioxane; 37% aqueous solution.
Preparative Methods: addition of H2SO4 to NaCl or 37% aqueous HCl.3
Handling, Storage, and Precautions: highly toxic and corrosive; handle only in a fume hood.
Bibliography
- 1(a)
Larock, R. C.;
Leong, W. W.
Comprehensive Organic Synthesis
1991,
4,
269.
10.1016/B978-0-08-052349-1.00096-2 Google Scholar(b) Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737.
- 2 Fogg, P. G. T.; Gerrard, W.; Clever, H. L. In Solubility Data Series; J. W. Lorimer; Ed.; Pergamon: Oxford, 1990; Vol. 42.
- 3(a)
Maxson, R. N.
Inorg. Synth.
1939,
1,
147.
10.1002/9780470132326.ch52 Google Scholar(b) Brown, H. C.; Rei, M.-H.; J. Org. Chem. 1966, 31, 1090.
- 4(a) Kropp, P. J.; Daus, K. A.; Crawford, S. D.; Tubergen, M. W.; Kepler, K. D.; Craig, S. L.; Wilson, V. P. J. Am. Chem. Soc. 1990, 112, 7433. (b) Kropp, P. J.; Daus, K. A.; Tubergen, M. W.; Kepler, K. D.; Wilson, V. P.; Craig, S. L.; Baillargeon, M. M.; Breton, G. W. J. Am. Chem. Soc. 1993, 115, 3071. (c) Kropp, P. J.; Crawford, S. D. J. Org. Chem. 1994, 59, 3102.
- 5(a) Shields, T. C. Can. J. Chem. 1971, 49, 1142. (b) Hassner, A.; Fibiger, R. F. Synthesis 1984, 960.
- 6(a) O'Connor, S. F.; Baldinger, L. H.; Vogt, R. R.; Hennion, G. F. J. Am. Chem. Soc. 1939, 61, 1454. (b) Hennion, G. F.; Irwin, C. F. J. Am. Chem. Soc. 1941, 63, 860.
- 7 For a different order, see: Brown, H. C.; Liu, K.-T.; J. Am. Chem. Soc. 1975, 97, 600.
- 8 Hudrlik, P. F.; Kulkarni, A. K.; Jain, S.; Hudrlik, A. M. Tetrahedron 1983, 39, 877.
- 9(a) Lucas, H. J.; Gould, C. W., Jr. J. Am. Chem. Soc. 1941, 63, 2541. (b) Buchanan, J. G.; Sable, H. Z. In Selective Organic Transformations; B. S. Thyagarajan, Ed.; Wiley: New York, 1972; Vol. 2, pp 1–92. (c) Armarego, W. L. F. In Stereochemistry of Heterocyclic Compounds; E. C. Taylor; A. Weissberger, Eds.; Wiley: New York, 1977; pp 23–25. (d) Bartok, M.; Lang, K. L. In The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulfur Analogues; S. Patai, Ed.; Wiley: New York, 1980; Part 2, pp 655–657.
- 10 Berti, G.; Macchia, B.; Macchia, F. Tetrahedron 1972, 28, 1299.
- 11 Lamaty, G.; Maloq, R.; Selve, C.; Sivade, A.; Wylde, J. J. Chem. Soc., Perkin Trans. 2 1975, 1119.
- 12(a) Copenhaver, J. E.; Whaley, A. M. Org. Synth., Coll. Vol. 1941, 1, 142. (b) Vogel, A. I. J. Chem. Soc 1943, 636. (c) Atwood, M. T. J. Am. Oil Chem. Soc. 1963, 40, 64.
- 13 Landini, D.; Montanari, F.; Rolla, F. Synthesis 1974, 37.
- 14 Fuchs, R.; Cole, L. L. Can. J. Chem. 1975, 53, 3620.
- 15(a) Norris, J. F.; Olmsted, A. W. Org. Synth., Coll. Vol. 1941, 1, 144. (b) Pourahmady, N.; Vickery, E. H.; Eisenbraun, E. J. J. Org. Chem. 1982, 47, 2590. (c) Melendez, E.; Pardo, M. C. BSF 1974, 632.
- 16 Conant, J. B.; Quayle, O. R. Org. Synth., Coll. Vol. 1941, 1, 292, 294.
- 17 Parham, W. E.; Sayed, Y. A. Synthesis 1976, 116.
- 18 Rao, C. G.; Rengaraju, S.; Bhatt, M. V. Chem. Commun./J. Chem. Soc., Chem. Commun. 1974, 584.
- 19(a)
McPhee, W. D.;
Klingsberg, E.
Org. Synth., Coll. Vol.
1955,
3,
119.
(b)
Dauben, W. G.;
Hiskey, C. F.;
Muhs, M. A.
J. Am. Chem. Soc.
1952,
74,
2082.
(c)
Van Atta, R. E.;
Zook, H. D.;
Elving, P. J.
J. Am. Chem. Soc.
1954,
76,
1185.
10.1021/ja01633a086 Google Scholar
- 20 Madesclaire, M. Tetrahedron 1988, 44, 6537.
- 21(a) Bhatt, M. V.; Kulkarni, S. U. Synthesis 1983, 249. (b) Brossi, A.; Blount, J. F.; O'Brien, J.; Teitel, S. J. Am. Chem. Soc. 1971, 93, 6248.
- 22 Olah, G. A.; Tolgyesi, W. S. In Friedel–Crafts and Related Reactions; G. A. Olah, Ed.; Interscience: New York, 1964; Vol. 2, Part 2, pp 1–92.
- 23(a) Marvel, C. S.; Porter, P. K. Org. Synth., Coll. Vol. 1932, 1, 377. (b) Grummitt, O.; Budewitz, E. P.; Chudd, C. C. Org. Synth., Coll. Vol. 1963, 4, 748. (c) Connor, D. S.; Klein, G. W.; Taylor, G. N.; Boeckman, R. K.; Medwid, J. B. Org. Synth., Coll. Vol. 1988, 6, 101.